HRID1158343

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：COCCCOc1cc(C(=O)N(C[C@H]2CN(C(=O)OC(C)(C)C)C[C@@H]2CN(C)C(=O)Cc2ccccc2)C(C)C)ccc1OC

HCID68616928

未命名化合物

PRODUCTS

生成物

HCID59512485

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID702

Ethanol

C2H6O

2 次

PROCEDURE

实验过程

Racemic (3R*,4R*)-3-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-4-[(methyl-phenylacetyl-amino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester is separated into the single enantiomers by preparative chiral HPLC on a Chiralpak AD-H column (4.6×250 mm, 5 μM particle size; flow rate 1 mL/min, UV=210 nM, injection=1.7 g in 5 mL ethanol and using ethanol as the eluent to give the enantiomerically pure title compound: tR (HPLC, Chiralpak AD-H, HPLC 250×4.6 mm, ethanol, flow: 0.5 ml/min): 26.46 min; and (3S,4S)-3-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-4-[(methyl-phenylacetyl-amino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester: tR (HPLC, Chiralpak AD-H, HPLC 250×4.6 mm, ethanol, flow: 0.5 ml/min): 13.53 min.

WORKUP

后处理

customRacemic (3R*,4R*)-3-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-4-[(methyl-phenylacetyl-amino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester is separated into the single enantiomers by preparative chiral HPLC on a Chiralpak AD-H column (4.6×250 mm, 5 μM particle size
customto give the enantiomerically pure title compound
custom26.46 min
custom13.53 min.

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-b9fc6f99bb294a2a8a5f9e4f3c0e9b2b
来源数据集: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07807709B2
来源说明: uspto-grants-2010_10

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([CH2:13][N:14]([CH3:24])[C:15](=[O:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:10]([CH2:25][N:26]([CH:43]([CH3:45])[CH3:44])[C:27](=[O:42])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH2:37][CH2:38][CH2:39][O:40][CH3:41])[CH:29]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH3:24])[C:15](=[O:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:10]([CH2:25][N:26]([CH:43]([CH3:45])[CH3:44])[C:27](=[O:42])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH2:37][CH2:38][CH2:39][O:40][CH3:41])[CH:29]=2)[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]