DE69809888T2 - Verfahren zur Herstellung von alpha-Aminoketonen - Google Patents
Verfahren zur Herstellung von alpha-AminoketonenInfo
- Publication number
- DE69809888T2 DE69809888T2 DE69809888T DE69809888T DE69809888T2 DE 69809888 T2 DE69809888 T2 DE 69809888T2 DE 69809888 T DE69809888 T DE 69809888T DE 69809888 T DE69809888 T DE 69809888T DE 69809888 T2 DE69809888 T2 DE 69809888T2
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- chloro
- carbamic acid
- oxopropyl
- benzyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title description 11
- -1 alcohol compound Chemical class 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 230000001603 reducing effect Effects 0.000 claims abstract description 22
- 150000003458 sulfonic acid derivatives Chemical class 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 27
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 12
- 125000006239 protecting group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 9
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 238000006722 reduction reaction Methods 0.000 claims description 9
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims description 9
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- VFHUZXQGMFOLRF-JTQLQIEISA-N methyl n-[(2s)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamate Chemical compound COC(=O)N[C@H](C(=O)CCl)CC1=CC=CC=C1 VFHUZXQGMFOLRF-JTQLQIEISA-N 0.000 claims description 3
- 150000002899 organoaluminium compounds Chemical class 0.000 claims description 3
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 2
- OYHLRJGDELITAF-INIZCTEOSA-N benzyl n-[(2s)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamate Chemical compound C([C@@H](C(=O)CCl)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 OYHLRJGDELITAF-INIZCTEOSA-N 0.000 claims description 2
- FIEZLSTZTKVKAT-LLVKDONJSA-N ethyl n-[(2r)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamate Chemical compound CCOC(=O)N[C@@H](C(=O)CCl)CC1=CC=CC=C1 FIEZLSTZTKVKAT-LLVKDONJSA-N 0.000 claims description 2
- CQXLRNNWSQJZRZ-NSHDSACASA-N ethyl n-[(2r)-4-chloro-3-oxo-1-phenylsulfanylbutan-2-yl]carbamate Chemical compound CCOC(=O)N[C@H](C(=O)CCl)CSC1=CC=CC=C1 CQXLRNNWSQJZRZ-NSHDSACASA-N 0.000 claims description 2
- FIEZLSTZTKVKAT-NSHDSACASA-N ethyl n-[(2s)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamate Chemical compound CCOC(=O)N[C@H](C(=O)CCl)CC1=CC=CC=C1 FIEZLSTZTKVKAT-NSHDSACASA-N 0.000 claims description 2
- CQXLRNNWSQJZRZ-LLVKDONJSA-N ethyl n-[(2s)-4-chloro-3-oxo-1-phenylsulfanylbutan-2-yl]carbamate Chemical compound CCOC(=O)N[C@@H](C(=O)CCl)CSC1=CC=CC=C1 CQXLRNNWSQJZRZ-LLVKDONJSA-N 0.000 claims description 2
- VFHUZXQGMFOLRF-SNVBAGLBSA-N methyl n-[(2r)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C(=O)CCl)CC1=CC=CC=C1 VFHUZXQGMFOLRF-SNVBAGLBSA-N 0.000 claims description 2
- KSRZEIAFVUNSKV-SNVBAGLBSA-N methyl n-[(2s)-4-chloro-3-oxo-1-phenylsulfanylbutan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C(=O)CCl)CSC1=CC=CC=C1 KSRZEIAFVUNSKV-SNVBAGLBSA-N 0.000 claims description 2
- VNENAWNFPWDTMZ-SECBINFHSA-N [(2r)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamic acid Chemical compound OC(=O)N[C@@H](C(=O)CCl)CC1=CC=CC=C1 VNENAWNFPWDTMZ-SECBINFHSA-N 0.000 claims 1
- FDRCIEKTDZMFKE-STQMWFEESA-N [(3s)-oxolan-3-yl] n-[(2s)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamate Chemical compound C([C@@H](C(=O)CCl)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 FDRCIEKTDZMFKE-STQMWFEESA-N 0.000 claims 1
- OYHLRJGDELITAF-MRXNPFEDSA-N benzyl n-[(2r)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamate Chemical compound C([C@H](C(=O)CCl)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 OYHLRJGDELITAF-MRXNPFEDSA-N 0.000 claims 1
- GHOXYLYITXKSDS-INIZCTEOSA-N benzyl n-[(2r)-4-chloro-3-oxo-1-phenylsulfanylbutan-2-yl]carbamate Chemical compound C([C@@H](C(=O)CCl)NC(=O)OCC=1C=CC=CC=1)SC1=CC=CC=C1 GHOXYLYITXKSDS-INIZCTEOSA-N 0.000 claims 1
- GHOXYLYITXKSDS-MRXNPFEDSA-N benzyl n-[(2s)-4-chloro-3-oxo-1-phenylsulfanylbutan-2-yl]carbamate Chemical compound C([C@H](C(=O)CCl)NC(=O)OCC=1C=CC=CC=1)SC1=CC=CC=C1 GHOXYLYITXKSDS-MRXNPFEDSA-N 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 239000003638 chemical reducing agent Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000013078 crystal Substances 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- GFGQSTIUFXHAJS-QWHCGFSZSA-N tert-butyl n-[(2s,3s)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]([C@H](O)CCl)CC1=CC=CC=C1 GFGQSTIUFXHAJS-QWHCGFSZSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- JAKDNFBATYIEIE-LBPRGKRZSA-N tert-butyl n-[(2s)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](C(=O)CCl)CC1=CC=CC=C1 JAKDNFBATYIEIE-LBPRGKRZSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 4
- YMCLVAZUQJPLTE-DLBZAZTESA-N benzyl n-[(2r,3s)-4-chloro-3-hydroxy-1-phenylsulfanylbutan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](CCl)O)NC(=O)OCC=1C=CC=CC=1)SC1=CC=CC=C1 YMCLVAZUQJPLTE-DLBZAZTESA-N 0.000 description 4
- 150000001728 carbonyl compounds Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000008206 alpha-amino acids Nutrition 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- NOUYQAAYWDNRNG-STQMWFEESA-N methyl (2s,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutanoate Chemical compound CC(C)(C)OC(=O)N[C@H]([C@H](O)C(=O)OC)CC1=CC=CC=C1 NOUYQAAYWDNRNG-STQMWFEESA-N 0.000 description 3
- ZAZXPIZQYVPWAW-WDEREUQCSA-N methyl n-[(2s,3s)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound COC(=O)N[C@H]([C@H](O)CCl)CC1=CC=CC=C1 ZAZXPIZQYVPWAW-WDEREUQCSA-N 0.000 description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
- 238000011916 stereoselective reduction Methods 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004030 hiv protease inhibitor Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- KCOPAESEGCGTKM-UHFFFAOYSA-N 1,3-oxazol-4-one Chemical compound O=C1COC=N1 KCOPAESEGCGTKM-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- RMQUNZQRHHMDIW-UHFFFAOYSA-N 2-chloroacetic acid;magnesium Chemical compound [Mg].OC(=O)CCl RMQUNZQRHHMDIW-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- YMCLVAZUQJPLTE-IRXDYDNUSA-N benzyl n-[(2r,3r)-4-chloro-3-hydroxy-1-phenylsulfanylbutan-2-yl]carbamate Chemical compound C([C@@H]([C@H](CCl)O)NC(=O)OCC=1C=CC=CC=1)SC1=CC=CC=C1 YMCLVAZUQJPLTE-IRXDYDNUSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
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- 238000004519 manufacturing process Methods 0.000 description 1
- NOUYQAAYWDNRNG-QWHCGFSZSA-N methyl (2r,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutanoate Chemical compound CC(C)(C)OC(=O)N[C@H]([C@@H](O)C(=O)OC)CC1=CC=CC=C1 NOUYQAAYWDNRNG-QWHCGFSZSA-N 0.000 description 1
- BSVHDHJWGZVKHH-LBPRGKRZSA-N methyl (3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxo-4-phenylbutanoate Chemical compound CC(C)(C)OC(=O)N[C@H](C(=O)C(=O)OC)CC1=CC=CC=C1 BSVHDHJWGZVKHH-LBPRGKRZSA-N 0.000 description 1
- ZAZXPIZQYVPWAW-QWRGUYRKSA-N methyl n-[(2s,3r)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound COC(=O)N[C@H]([C@@H](O)CCl)CC1=CC=CC=C1 ZAZXPIZQYVPWAW-QWRGUYRKSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
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- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- GLDHIVIONXFFQT-LBPRGKRZSA-N tert-butyl n-[(2r)-4-chloro-3-oxo-1-phenylsulfanylbutan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](C(=O)CCl)CSC1=CC=CC=C1 GLDHIVIONXFFQT-LBPRGKRZSA-N 0.000 description 1
- GLDHIVIONXFFQT-GFCCVEGCSA-N tert-butyl n-[(2s)-4-chloro-3-oxo-1-phenylsulfanylbutan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](C(=O)CCl)CSC1=CC=CC=C1 GLDHIVIONXFFQT-GFCCVEGCSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16200597 | 1997-06-03 | ||
| JP21928797 | 1997-07-29 | ||
| PCT/JP1998/002444 WO1998055452A1 (fr) | 1997-06-03 | 1998-06-03 | PROCEDE DE REDUCTION D'α-AMINO CETONES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69809888D1 DE69809888D1 (de) | 2003-01-16 |
| DE69809888T2 true DE69809888T2 (de) | 2003-08-28 |
Family
ID=26487946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69809888T Expired - Lifetime DE69809888T2 (de) | 1997-06-03 | 1998-06-03 | Verfahren zur Herstellung von alpha-Aminoketonen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6255522B1 (https=) |
| EP (1) | EP0969000B1 (https=) |
| KR (1) | KR100517772B1 (https=) |
| CN (1) | CN1128135C (https=) |
| AT (1) | ATE229000T1 (https=) |
| CA (1) | CA2262966C (https=) |
| DE (1) | DE69809888T2 (https=) |
| ES (1) | ES2189169T3 (https=) |
| IN (1) | IN184319B (https=) |
| WO (1) | WO1998055452A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN184319B (https=) | 1997-06-03 | 2000-08-05 | Kaneka Corp | |
| JP4143787B2 (ja) * | 1999-07-28 | 2008-09-03 | 味の素株式会社 | α−アミノハロメチルケトン誘導体の製造方法 |
| WO2002044136A1 (en) * | 2000-11-30 | 2002-06-06 | Ajinomoto Co., Inc. | PROCESSES FOR PREPARATION OF N-PROTECTED-ss-AMINO ALCOHOLS AND N-PROTECTED-ss-AMINO EPOXIDES |
| WO2002070714A1 (en) * | 2001-03-02 | 2002-09-12 | Daiichi Fine Chemical Co., Ltd. | Aminoketone asymmetric reductase and nucleic acid thereof |
| AU2003241747A1 (en) * | 2002-06-11 | 2003-12-22 | Kaneka Corporation | PROCESS FOR PRODUCING OPTICALLY ACTIVE ss-AMINO ALCOHOL |
| CN100436412C (zh) * | 2004-07-06 | 2008-11-26 | 厦门大学 | 硼氢化物-酸还原体系还原氨基酮衍生物制备相应氨基醇的方法 |
| CN102766074B (zh) * | 2012-08-07 | 2014-05-07 | 江西东邦药业有限公司 | 抗艾滋病药物中间体的制备方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5523266B2 (https=) * | 1974-04-23 | 1980-06-21 | ||
| JPS54154739A (en) * | 1978-05-26 | 1979-12-06 | Ono Pharmaceut Co Ltd | Reducing agents |
| US4745204A (en) * | 1986-06-05 | 1988-05-17 | International Business Machines Corporation | Process for producing aluminum alkoxide or aluminum aryloxide |
| JPS632935A (ja) * | 1986-06-20 | 1988-01-07 | Sumitomo Chem Co Ltd | 光学活性アルコ−ル類の製造方法 |
| JPH0723332B2 (ja) * | 1987-05-29 | 1995-03-15 | 旭化成工業株式会社 | １，３−ジクロル−２−プロパノ−ルの製造法 |
| JP2804284B2 (ja) * | 1988-03-23 | 1998-09-24 | 三共株式会社 | ４―アミノ―３―ヒドロキシカルボン酸類の立体選択的合成法 |
| JP2847584B2 (ja) * | 1991-06-21 | 1999-01-20 | 高砂香料工業株式会社 | シクロヘキシル酪酸誘導体及びその製造法 |
| JPH0525107A (ja) * | 1991-07-19 | 1993-02-02 | Nippon Kayaku Co Ltd | 光学活性α−ヒドロキシ−βーアミノ酸エステルのラセミ化法 |
| JPH07165678A (ja) * | 1993-12-08 | 1995-06-27 | Kanegafuchi Chem Ind Co Ltd | ニトロオレフィン化合物 |
| JPH0812629A (ja) * | 1994-06-28 | 1996-01-16 | Kanegafuchi Chem Ind Co Ltd | 光学活性ジヒドロキシアミン誘導体の製造法及びその中間体 |
| US5475138A (en) * | 1994-07-07 | 1995-12-12 | Pharm-Eco Laboratories Incorporated | Method preparing amino acid-derived diaminopropanols |
| US5523463A (en) * | 1994-09-23 | 1996-06-04 | Hoffmann-La Roche Inc. | Method of producing halogenated and alpha-aminoalchohols |
| JPH08143517A (ja) * | 1994-11-18 | 1996-06-04 | Nippon Kayaku Co Ltd | 光学活性３−アミノ−１，２−ブタンジオール誘導体の製造法 |
| JPH08198837A (ja) * | 1995-01-25 | 1996-08-06 | Mitsubishi Chem Corp | ２−アミノ−１−アルカノール誘導体の製造方法 |
| JP3855323B2 (ja) * | 1995-11-17 | 2006-12-06 | 味の素株式会社 | ３−アミノ−２−オキソ−１−ハロゲノプロパン誘導体の製造方法 |
| HUP9800085A3 (en) * | 1996-01-29 | 1998-06-29 | Kaneka Corp | Processes for the reduction of carbonyl compounds and producing alfa-amino-alcohol derivatives |
| HUP9903874A3 (en) | 1996-09-13 | 2000-06-28 | Nippon Kayaku Kk | Optically active erythro-3-amino-2-hydroxybutyric esters and process for preparing said esters |
| IN184319B (https=) | 1997-06-03 | 2000-08-05 | Kaneka Corp |
-
1998
- 1998-05-28 IN IN952CA1998 patent/IN184319B/en unknown
- 1998-06-03 AT AT98923095T patent/ATE229000T1/de not_active IP Right Cessation
- 1998-06-03 CN CN98800734A patent/CN1128135C/zh not_active Expired - Fee Related
- 1998-06-03 CA CA002262966A patent/CA2262966C/en not_active Expired - Fee Related
- 1998-06-03 ES ES98923095T patent/ES2189169T3/es not_active Expired - Lifetime
- 1998-06-03 US US09/230,887 patent/US6255522B1/en not_active Expired - Lifetime
- 1998-06-03 WO PCT/JP1998/002444 patent/WO1998055452A1/ja not_active Ceased
- 1998-06-03 KR KR10-1999-7000582A patent/KR100517772B1/ko not_active Expired - Fee Related
- 1998-06-03 DE DE69809888T patent/DE69809888T2/de not_active Expired - Lifetime
- 1998-06-03 EP EP98923095A patent/EP0969000B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0969000B1 (en) | 2002-12-04 |
| US6255522B1 (en) | 2001-07-03 |
| CA2262966A1 (en) | 1998-12-10 |
| EP0969000A1 (en) | 2000-01-05 |
| EP0969000A4 (en) | 2000-07-12 |
| IN184319B (https=) | 2000-08-05 |
| KR100517772B1 (ko) | 2005-09-29 |
| ES2189169T3 (es) | 2003-07-01 |
| CN1128135C (zh) | 2003-11-19 |
| ATE229000T1 (de) | 2002-12-15 |
| CN1228081A (zh) | 1999-09-08 |
| CA2262966C (en) | 2007-09-18 |
| WO1998055452A1 (fr) | 1998-12-10 |
| KR20000068016A (ko) | 2000-11-25 |
| DE69809888D1 (de) | 2003-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |