DE4008856A1 - Verfahren zur herstellung von acylalen - Google Patents
Verfahren zur herstellung von acylalenInfo
- Publication number
- DE4008856A1 DE4008856A1 DE4008856A DE4008856A DE4008856A1 DE 4008856 A1 DE4008856 A1 DE 4008856A1 DE 4008856 A DE4008856 A DE 4008856A DE 4008856 A DE4008856 A DE 4008856A DE 4008856 A1 DE4008856 A1 DE 4008856A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- groups
- acetoxymethoxy
- formula
- hydrogen
- 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.)
- Withdrawn
Links
- 150000008063 acylals Chemical class 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 8
- -1 benzyloxy, benzylthio, benzylamino, dibenzylamino Chemical group 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000005035 acylthio group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000005544 phthalimido group Chemical group 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960004132 diethyl ether Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229940052303 ethers for general anesthesia Drugs 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- AJJGRBMYVRSEES-UHFFFAOYSA-N 1,3-di(propan-2-yloxy)propan-2-ol Chemical compound CC(C)OCC(O)COC(C)C AJJGRBMYVRSEES-UHFFFAOYSA-N 0.000 description 1
- AZOGDLWDLMZAAN-UHFFFAOYSA-N 1,3-di(propan-2-yloxy)propan-2-yloxymethyl acetate Chemical compound CC(C)OCC(COC(C)C)OCOC(C)=O AZOGDLWDLMZAAN-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NWLUZGJDEZBBRH-UHFFFAOYSA-N 2-(propan-2-yloxymethyl)oxirane Chemical compound CC(C)OCC1CO1 NWLUZGJDEZBBRH-UHFFFAOYSA-N 0.000 description 1
- MEJXGECPYZGPPN-UHFFFAOYSA-N 2-methylphosphonoyloxypropane Chemical compound CC(C)OP(C)=O MEJXGECPYZGPPN-UHFFFAOYSA-N 0.000 description 1
- ITRNNLCTHQEATJ-UHFFFAOYSA-N C(C)(=O)OCOCCOC(C)=O.C(C)(=O)OCOCCOC1=CC=CC=C1.C(C)(=O)OCOCCOCC1=CC=CC=C1.C(C)(=O)OCOCCOCCCC.C(C1=CC=CC=C1)(=O)OCOCCOC(C)C Chemical compound C(C)(=O)OCOCCOC(C)=O.C(C)(=O)OCOCCOC1=CC=CC=C1.C(C)(=O)OCOCCOCC1=CC=CC=C1.C(C)(=O)OCOCCOCCCC.C(C1=CC=CC=C1)(=O)OCOCCOC(C)C ITRNNLCTHQEATJ-UHFFFAOYSA-N 0.000 description 1
- JODRSXUEGXBEBL-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OCOCC(COC(C)C)OCC1=CC=CC=C1.C(C)(=O)OCOCC(COC(C)C)OCC1=CC=CC=C1.C(C)(C)OP(OC(C)C)(=O)CCCOCOC(C)=O Chemical compound C(C1=CC=CC=C1)(=O)OCOCC(COC(C)C)OCC1=CC=CC=C1.C(C)(=O)OCOCC(COC(C)C)OCC1=CC=CC=C1.C(C)(C)OP(OC(C)C)(=O)CCCOCOC(C)=O JODRSXUEGXBEBL-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001521416 Leva Species 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- UYZUZNGAVJUFEH-UHFFFAOYSA-N acetyloxymethylsulfanylmethoxymethylsulfanylmethyl acetate Chemical compound CC(=O)OCSCOCSCOC(C)=O UYZUZNGAVJUFEH-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4008856A DE4008856A1 (de) | 1990-03-20 | 1990-03-20 | Verfahren zur herstellung von acylalen |
| ES91104127T ES2068410T3 (es) | 1990-03-20 | 1991-03-18 | Procedimiento para la preparacion de acilales. |
| DK91104127.5T DK0448006T3 (da) | 1990-03-20 | 1991-03-18 | Fremgangsmåde til fremstilling af acylaler |
| EP91104127A EP0448006B1 (de) | 1990-03-20 | 1991-03-18 | Verfahren zur Herstellung von Acylalen |
| DE59104352T DE59104352D1 (de) | 1990-03-20 | 1991-03-18 | Verfahren zur Herstellung von Acylalen. |
| US07/671,103 US5231221A (en) | 1990-03-20 | 1991-03-18 | Process for the preparation of acylals |
| AT91104127T ATE117670T1 (de) | 1990-03-20 | 1991-03-18 | Verfahren zur herstellung von acylalen. |
| JP3078291A JP3010076B2 (ja) | 1990-03-20 | 1991-03-19 | アシラールの製造方法 |
| PT97072A PT97072A (pt) | 1990-03-20 | 1991-03-19 | Processo para a preparacao de acilais |
| IE090791A IE910907A1 (en) | 1990-03-20 | 1991-03-19 | Process for the preparation of acylals |
| TW080102324A TW206211B (enExample) | 1990-03-20 | 1991-03-26 | |
| GR950400320T GR3015102T3 (en) | 1990-03-20 | 1995-02-17 | Process for the preparation of acylales. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4008856A DE4008856A1 (de) | 1990-03-20 | 1990-03-20 | Verfahren zur herstellung von acylalen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4008856A1 true DE4008856A1 (de) | 1991-09-26 |
Family
ID=6402600
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4008856A Withdrawn DE4008856A1 (de) | 1990-03-20 | 1990-03-20 | Verfahren zur herstellung von acylalen |
| DE59104352T Expired - Fee Related DE59104352D1 (de) | 1990-03-20 | 1991-03-18 | Verfahren zur Herstellung von Acylalen. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59104352T Expired - Fee Related DE59104352D1 (de) | 1990-03-20 | 1991-03-18 | Verfahren zur Herstellung von Acylalen. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5231221A (enExample) |
| EP (1) | EP0448006B1 (enExample) |
| JP (1) | JP3010076B2 (enExample) |
| AT (1) | ATE117670T1 (enExample) |
| DE (2) | DE4008856A1 (enExample) |
| DK (1) | DK0448006T3 (enExample) |
| ES (1) | ES2068410T3 (enExample) |
| GR (1) | GR3015102T3 (enExample) |
| IE (1) | IE910907A1 (enExample) |
| PT (1) | PT97072A (enExample) |
| TW (1) | TW206211B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4444669A1 (de) * | 1994-12-15 | 1996-06-20 | Hoechst Ag | Strahlungsempfindliches Gemisch |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB830850A (en) * | 1957-11-07 | 1960-03-23 | Distillers Co Yeast Ltd | Production of alkoxymethyl acetates |
| US3165532A (en) * | 1961-06-14 | 1965-01-12 | Exxon Research Engineering Co | Hemiacetal ester production |
-
1990
- 1990-03-20 DE DE4008856A patent/DE4008856A1/de not_active Withdrawn
-
1991
- 1991-03-18 ES ES91104127T patent/ES2068410T3/es not_active Expired - Lifetime
- 1991-03-18 EP EP91104127A patent/EP0448006B1/de not_active Expired - Lifetime
- 1991-03-18 US US07/671,103 patent/US5231221A/en not_active Expired - Fee Related
- 1991-03-18 DK DK91104127.5T patent/DK0448006T3/da active
- 1991-03-18 DE DE59104352T patent/DE59104352D1/de not_active Expired - Fee Related
- 1991-03-18 AT AT91104127T patent/ATE117670T1/de not_active IP Right Cessation
- 1991-03-19 JP JP3078291A patent/JP3010076B2/ja not_active Expired - Lifetime
- 1991-03-19 PT PT97072A patent/PT97072A/pt not_active Application Discontinuation
- 1991-03-19 IE IE090791A patent/IE910907A1/en unknown
- 1991-03-26 TW TW080102324A patent/TW206211B/zh active
-
1995
- 1995-02-17 GR GR950400320T patent/GR3015102T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR3015102T3 (en) | 1995-05-31 |
| DE59104352D1 (de) | 1995-03-09 |
| PT97072A (pt) | 1991-12-31 |
| DK0448006T3 (da) | 1995-06-19 |
| IE910907A1 (en) | 1991-09-25 |
| EP0448006A2 (de) | 1991-09-25 |
| JP3010076B2 (ja) | 2000-02-14 |
| JPH04217941A (ja) | 1992-08-07 |
| ES2068410T3 (es) | 1995-04-16 |
| ATE117670T1 (de) | 1995-02-15 |
| TW206211B (enExample) | 1993-05-21 |
| EP0448006A3 (en) | 1992-04-22 |
| EP0448006B1 (de) | 1995-01-25 |
| US5231221A (en) | 1993-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |