HRID1941334

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID15908

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

C8H17N3

HCID2734891

Methyl tryptophanate hydrochloride

C12H15ClN2O2

结构：Cc1cc(C)cc(C(=O)N(C)[C@@H](Cc2ccc(-c3ccno3)cc2)C(=O)O)c1

HCID18663506

未命名化合物

HCID178418300

未命名化合物

PRODUCTS

生成物

结构：COC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1ccc(-c2ccno2)cc1)N(C)C(=O)c1cc(C)cc(C)c1

HCID70092623

未命名化合物

HCID70094113

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

At 0° C., N-(3,5-dimethylbenzoyl)-N-methyl-3-[4-(5-isoxazolyl)-phenyl]-alanine (445 mg) is stirred in N,N-dimethylformamide (24 ml) together with (L)-tryptophane methyl ester hydrochloride (400 mg), hydroxybenztriazol (330 mg), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.32 ml) for 1 hour and at ambient temperature over night. After extraction with ethyl acetate and 10% aqueous citric acid the organic phase is washed with 4% aqueous sodium bicarbonate, and with brine, dried and evaporated. Flash chromatography on silica gel (hexane/ethyl acetate 2:1) gives the product as a mixture of diastereoisomer. Separation by medium pressure chromatography on a silica gel column, using ether/dichloromethane (1:1) as solvent gives both [N-(3,5-dimethylbenzoyl)-N-methyl-3-[4-(5-isoxazolyl)-phenyl]-(D)-alanyl]-(L)-tryptophane methyl ester, and [N-(3,5-dimethylbenzoyl)-N-methyl-3-[4-(5-isoxazolyl)-phenyl]-(L)-alanyl]-(L)-tryptophane methyl ester.

WORKUP

后处理

extractionAfter extraction with ethyl acetate and 10% aqueous citric acid the organic phase
washis washed with 4% aqueous sodium bicarbonate
dry with materialwith brine, dried
customevaporated
customFlash chromatography on silica gel (hexane/ethyl acetate 2:1) gives the product
additionas a mixture of diastereoisomer
customSeparation by medium pressure chromatography on a silica gel column

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-3ad284645618494fa43ad05884973e4c
来源数据集: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05703106
来源说明: uspto-grants-1997_12

反应 SMILES

[CH3:1][C:2]1[CH:3]=[C:4]([CH:25]=[C:26]([CH3:28])[CH:27]=1)[C:5]([N:7]([CH3:24])[C@H:8]([C:21]([OH:23])=[O:22])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:20][N:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)=[O:6].Cl.[CH3:30][O:31][C:32](=[O:45])[C@H:33]([CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH:38][CH:37]=1)[NH2:34].OC1C2N=NNC=2C=CC=1.CN(C)CCCN=C=NCC>CN(C)C=O>[CH3:30][O:31][C:32](=[O:45])[C@H:33]([CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH:38][CH:37]=1)[NH:34][C:21](=[O:23])[C@@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:20][N:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[N:7]([C:5](=[O:6])[C:4]1[CH:3]=[C:2]([CH3:1])[CH:27]=[C:26]([CH3:28])[CH:25]=1)[CH3:24].[CH3:30][O:31][C:32](=[O:45])[C@H:33]([CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH:38][CH:37]=1)[NH:34][C:21](=[O:22])[C@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:20][N:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[N:7]([C:5](=[O:6])[C:4]1[CH:3]=[C:2]([CH3:1])[CH:27]=[C:26]([CH3:28])[CH:25]=1)[CH3:24]