CN106008271B - 一种谷氨酸-1-叔丁酯衍生物的制备方法 - Google Patents
一种谷氨酸-1-叔丁酯衍生物的制备方法 Download PDFInfo
- Publication number
- CN106008271B CN106008271B CN201610370118.2A CN201610370118A CN106008271B CN 106008271 B CN106008271 B CN 106008271B CN 201610370118 A CN201610370118 A CN 201610370118A CN 106008271 B CN106008271 B CN 106008271B
- Authority
- CN
- China
- Prior art keywords
- glutamic acid
- tert
- glu
- otbu
- butyl
- 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.)
- Active
Links
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 title claims abstract description 180
- 235000013922 glutamic acid Nutrition 0.000 title claims abstract description 101
- 239000004220 glutamic acid Substances 0.000 title claims abstract description 101
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 title claims abstract description 83
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 57
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 21
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical class OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 10
- 150000003624 transition metals Chemical class 0.000 claims abstract description 8
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract 5
- QVAQMUAKTNUNLN-LURJTMIESA-N (4s)-4-amino-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid Chemical compound CC(C)(C)OC(=O)[C@@H](N)CCC(O)=O QVAQMUAKTNUNLN-LURJTMIESA-N 0.000 claims description 41
- 150000002220 fluorenes Chemical class 0.000 claims description 36
- 125000002252 acyl group Chemical group 0.000 claims description 33
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 33
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 24
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 16
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 229960002317 succinimide Drugs 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
- 125000004989 dicarbonyl group Chemical group 0.000 claims description 11
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- -1 benzene methoxy carbonyl acyl succinyl Imines Chemical class 0.000 claims description 7
- 238000009826 distribution Methods 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 5
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical group [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 5
- 229910000366 copper(II) sulfate Inorganic materials 0.000 claims description 5
- 238000005809 transesterification reaction Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical class CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 4
- 229910021592 Copper(II) chloride Inorganic materials 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- BBJIPMIXTXKYLZ-UHFFFAOYSA-N isoglutamic acid Chemical compound OC(=O)CC(N)CC(O)=O BBJIPMIXTXKYLZ-UHFFFAOYSA-N 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 4
- 102000004196 processed proteins & peptides Human genes 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000010949 copper Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000007171 acid catalysis Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- OIOAKXPMBIZAHL-LURJTMIESA-N (2s)-2-azaniumyl-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoate Chemical compound CC(C)(C)OC(=O)CC[C@H](N)C(O)=O OIOAKXPMBIZAHL-LURJTMIESA-N 0.000 description 5
- GOPWHXPXSPIIQZ-FQEVSTJZSA-N (4s)-4-(9h-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CCC(O)=O)C(=O)OC(C)(C)C)C3=CC=CC=C3C2=C1 GOPWHXPXSPIIQZ-FQEVSTJZSA-N 0.000 description 4
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 4
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- MJSHDCCLFGOEIK-UHFFFAOYSA-N benzyl (2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)OCC1=CC=CC=C1 MJSHDCCLFGOEIK-UHFFFAOYSA-N 0.000 description 3
- 229910052927 chalcanthite Inorganic materials 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- PVFCXMDXBIEMQG-JTQLQIEISA-N (2s)-2-(phenylmethoxycarbonylamino)pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 PVFCXMDXBIEMQG-JTQLQIEISA-N 0.000 description 2
- WHNQTHDJEZTVHS-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)propanoic acid Chemical compound C1=CC=C2SC(CCC(=O)O)=NC2=C1 WHNQTHDJEZTVHS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 229960004217 benzyl alcohol Drugs 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000003223 protective agent Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- YMOYURYWGUWMFM-VIFPVBQESA-N (4s)-5-[(2-methylpropan-2-yl)oxy]-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](CCC(O)=O)C(=O)OC(C)(C)C YMOYURYWGUWMFM-VIFPVBQESA-N 0.000 description 1
- SHLDRGRIHSAHQU-UHFFFAOYSA-N C(O)(O)=O.C(OC(C)(C)C)(OC(C)(C)C)=O Chemical compound C(O)(O)=O.C(OC(C)(C)C)(OC(C)(C)C)=O SHLDRGRIHSAHQU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- GZDFHIJNHHMENY-UHFFFAOYSA-N Dimethyl dicarbonate Chemical compound COC(=O)OC(=O)OC GZDFHIJNHHMENY-UHFFFAOYSA-N 0.000 description 1
- YSDQQAXHVYUZIW-QCIJIYAXSA-N Liraglutide Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCNC(=O)CC[C@H](NC(=O)CCCCCCCCCCCCCCC)C(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=C(O)C=C1 YSDQQAXHVYUZIW-QCIJIYAXSA-N 0.000 description 1
- 108010019598 Liraglutide Proteins 0.000 description 1
- NASRDENTZCCAPN-UHFFFAOYSA-N OC([Na])=O Chemical class OC([Na])=O NASRDENTZCCAPN-UHFFFAOYSA-N 0.000 description 1
- 108010078233 Thymalfasin Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 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
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000004316 dimethyl dicarbonate Substances 0.000 description 1
- 235000010300 dimethyl dicarbonate Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- IRXSLJNXXZKURP-UHFFFAOYSA-N fluorenylmethyloxycarbonyl chloride Chemical compound C1=CC=C2C(COC(=O)Cl)C3=CC=CC=C3C2=C1 IRXSLJNXXZKURP-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229960002701 liraglutide Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 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
- C07C269/04—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 from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
序号 | 名称 | 英文缩写 |
1 | 谷氨酸-5-叔丁酯 | Glu(OtBu) |
2 | 谷氨酸-1-叔丁酯 | Glu-OtBu |
3 | 谷氨酸-5-叔丁酯铜螯合物 | Cu[Glu(OtBu)]x |
4 | 谷氨酸-1-叔丁酯铜螯合物 | Cu(Glu-OtBu)x |
5 | 芴甲氧羰酰琥珀酰亚胺 | Fmoc-OSu |
6 | 芴甲氧羰酰氯 | Fmoc-Cl |
7 | 二碳酸二叔丁酯 | (Boc)2O |
8 | 苯甲氧羰酰琥珀酰亚胺 | CbzOSu |
9 | 谷氨酸 | Glu |
10 | 谷氨酸双叔丁酯 | Glu(OtBu)2 |
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610370118.2A CN106008271B (zh) | 2016-05-27 | 2016-05-27 | 一种谷氨酸-1-叔丁酯衍生物的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610370118.2A CN106008271B (zh) | 2016-05-27 | 2016-05-27 | 一种谷氨酸-1-叔丁酯衍生物的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN106008271A CN106008271A (zh) | 2016-10-12 |
CN106008271B true CN106008271B (zh) | 2018-06-19 |
Family
ID=57092628
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610370118.2A Active CN106008271B (zh) | 2016-05-27 | 2016-05-27 | 一种谷氨酸-1-叔丁酯衍生物的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN106008271B (zh) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109180533A (zh) * | 2018-09-25 | 2019-01-11 | 四川什邡市三高生化实业有限公司 | 一种n-9-芴甲氧羰基-d-天门冬氨酸-4-叔丁酯 |
CN109516925B (zh) * | 2018-10-31 | 2021-07-16 | 陕西慧康生物科技有限责任公司 | 一种谷氨酸-1-甲酯-5-叔丁酯的合成方法 |
CN113896657A (zh) * | 2021-11-16 | 2022-01-07 | 山东盛安贝新能源有限公司南京分公司 | 一种索马鲁肽保护氨基酸的合成方法及纯化方法 |
CN115504893B (zh) * | 2022-11-18 | 2023-03-10 | 成都普康生物科技有限公司 | 一种L-谷氨酸-α-叔丁酯的合成方法 |
CN116178214B (zh) * | 2022-12-08 | 2024-03-26 | 吉尔生化(上海)有限公司 | 一种n-(9-芴甲氧羰基)-谷氨酸-1-叔丁酯的制备方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1323269A (zh) * | 1998-08-31 | 2001-11-21 | 布莱阿姆青年大学 | 带有靴座定位柔性件的制动装置 |
CN103232370B (zh) * | 2013-05-09 | 2015-09-30 | 成都郑源生化科技有限公司 | 一种芴甲氧羰酰天冬氨酸-4-叔丁酯的制备方法 |
CN105541649A (zh) * | 2015-12-17 | 2016-05-04 | 吉尔生化(上海)有限公司 | 一种谷氨酸-5-苄酯-1-叔丁酯盐酸盐的制备方法 |
-
2016
- 2016-05-27 CN CN201610370118.2A patent/CN106008271B/zh active Active
Also Published As
Publication number | Publication date |
---|---|
CN106008271A (zh) | 2016-10-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN106008271B (zh) | 一种谷氨酸-1-叔丁酯衍生物的制备方法 | |
CN104974072B (zh) | 一种制备西洛多辛中间体的方法 | |
CN108047077B (zh) | 一种奥司他韦手性杂质的制备方法 | |
CN104356197B (zh) | 一种卡非佐米中间体及其制备方法,以及一种卡非佐米的制备方法 | |
CN104379558B (zh) | 利用谷氨酸衍生物和羟基苯胺或羟基被保护的羟基苯胺合成拉马琳以及拉马琳前体的方法 | |
KR101182334B1 (ko) | 라말린의 합성방법 | |
CN105884628B (zh) | 2,4-二叔丁基-5-氨基酚的制备方法 | |
CN107353222A (zh) | 制备2‑氨基‑n‑(2,2,2‑三氟乙基)乙酰胺的方法 | |
CN106045883B (zh) | 一种天冬氨酸-1-叔丁酯衍生物的制备方法 | |
CN107674062B (zh) | 抗丙肝药物中间体、制备方法及应用 | |
CN107629001B (zh) | 一种抗癌药物乐伐替尼的合成方法 | |
CN107739400A (zh) | 一种赖氨酸二肽的合成方法 | |
CN113735716B (zh) | 一种亚精胺的制备方法 | |
CN112939814B (zh) | 一种氘代达卡他韦中间体的制备方法 | |
CN109053839A (zh) | 核苷修饰物3’-O-CH2N3-2’-O-Me-胞嘧啶核苷的新型制备方法 | |
CN111484418B (zh) | 4-氨基-2-环戊烯-1-甲醇盐酸盐的制备方法 | |
EP3398933B1 (en) | Method for preparing long-chain compound | |
CN104788353B (zh) | 一种合成4‑氧代‑l‑脯氨酸衍生物的方法 | |
CN106866657A (zh) | 一种麦角新碱的制备方法 | |
JP2018039773A (ja) | 含窒素9員環アルキン | |
CN111116477A (zh) | 多拉米胺的合成工艺 | |
CN112679567B (zh) | 1n,3n-异帕米星的合成方法 | |
CN109678738A (zh) | 一种合成(2s,3s)-3-氨基-二环[2.2.2]辛烷-2-甲酸酯的方法 | |
CN109970620A (zh) | 一种制备沙格列汀中间体的方法 | |
CN107129437A (zh) | 4-[(2-氯乙基-2-羟乙基)氨基-]-l-苯丙氨酸盐酸盐的制备方法与应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A preparation method of 1-tert-butyl glutamate derivative Effective date of registration: 20230105 Granted publication date: 20180619 Pledgee: Chengdu Rural Commercial Bank Co.,Ltd. Pujiang Xilai Guzhen Sub branch Pledgor: CHENGDU ZHENGYUAN BIOCHEMICAL TECHNOLOGY CO.,LTD. Registration number: Y2023510000001 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20231228 Granted publication date: 20180619 Pledgee: Chengdu Rural Commercial Bank Co.,Ltd. Pujiang Xilai Guzhen Sub branch Pledgor: CHENGDU ZHENGYUAN BIOCHEMICAL TECHNOLOGY CO.,LTD. Registration number: Y2023510000001 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of a derivative of glutamic acid 1-tert butyl ester Granted publication date: 20180619 Pledgee: Chengdu Rural Commercial Bank Co.,Ltd. Pujiang Xilai Guzhen Sub branch Pledgor: CHENGDU ZHENGYUAN BIOCHEMICAL TECHNOLOGY CO.,LTD. Registration number: Y2024510000001 |