HRID391950

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11

1,2-Dichloroethane

C2H4Cl2

结构：CC(C)(C)OC(=O)N[C@H]1CC[C@@H](C(=O)O)C1

HCID1512526

(1R,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylic acid

C11H19NO4

结构：COC(=O)[C@H](Cc1ccc(-c2ccnc(C)c2C)cc1)NC(=O)[C@@H]1Cc2cc3c(cc2CN1)O[C@@H](c1ccc(OCc2ccc(Cl)c(Cl)c2)cc1)CO3

HCID58327416

未命名化合物

PRODUCTS

生成物

结构：Cc1nccc(-c2ccc(C[C@H](NC(=O)[C@@H]3Cc4cc5c(cc4CN3C(=O)[C@@H]3CC[C@H](NC(=O)OC(C)(C)C)C3)O[C@@H](c3ccc(OCc4ccc(Cl)c(Cl)c4)cc3)CO5)C(=O)O)cc2)c1C

HCID58327133

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

EDC (3 eq.) and (1R,3S)-3-tert-butoxycarbonylamino-cyclopentanecarboxylic acid (6 eq.) were dissolved in DCM and stirred for 40 minutes. To this solution was added (S)-2-({(3S,8S)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-3-[4-(2,3-dimethyl-pyridin-4-yl)-phenyl]-propionic acid methyl ester (25 mg) and stirred for 12 hours. The reaction mixture was directly purified over silica (hexanes to 1:1 hexanes EtOAc to 1:1 hexanes EtOAc+1% MeOH to 1:1 hexanes EtOAc+2% MeOH to 1:1 hexanes EtOAc+3% MeOH). The resulting compound was hydrolyzed according to General Procedure B to give the title compound. LCMS (m/z): 950.

WORKUP

后处理

stirringstirred for 12 hours
customThe reaction mixture was directly purified over silica (hexanes to 1:1 hexanes EtOAc to 1:1 hexanes EtOAc+1% MeOH to 1:1 hexanes EtOAc+2% MeOH to 1:1 hexanes EtOAc+3% MeOH)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-76b41c96a6da486e9baf16d5a135798a
来源数据集: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08383644B2
来源说明: uspto-grants-2013_02

反应 SMILES

C(Cl)CCl.[C:5]([O:9][C:10]([NH:12][C@H:13]1[CH2:17][CH2:16][C@@H:15]([C:18]([OH:20])=O)[CH2:14]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].C[O:22][C:23](=[O:73])[C@@H:24]([NH:40][C:41]([C@@H:43]1[CH2:52][C:51]2[CH:50]=[C:49]3[O:53][CH2:54][C@H:55]([C:57]4[CH:62]=[CH:61][C:60]([O:63][CH2:64][C:65]5[CH:70]=[CH:69][C:68]([Cl:71])=[C:67]([Cl:72])[CH:66]=5)=[CH:59][CH:58]=4)[O:56][C:48]3=[CH:47][C:46]=2[CH2:45][NH:44]1)=[O:42])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][N:35]=[C:34]([CH3:38])[C:33]=2[CH3:39])=[CH:28][CH:27]=1>C(Cl)Cl>[C:5]([O:9][C:10]([NH:12][C@H:13]1[CH2:17][CH2:16][C@@H:15]([C:18]([N:44]2[C@H:43]([C:41]([NH:40][C@@H:24]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([C:32]4[CH:37]=[CH:36][N:35]=[C:34]([CH3:38])[C:33]=4[CH3:39])=[CH:30][CH:31]=3)[C:23]([OH:73])=[O:22])=[O:42])[CH2:52][C:51]3[CH:50]=[C:49]4[O:53][CH2:54][C@H:55]([C:57]5[CH:62]=[CH:61][C:60]([O:63][CH2:64][C:65]6[CH:70]=[CH:69][C:68]([Cl:71])=[C:67]([Cl:72])[CH:66]=6)=[CH:59][CH:58]=5)[O:56][C:48]4=[CH:47][C:46]=3[CH2:45]2)=[O:20])[CH2:14]1)=[O:11])([CH3:6])([CH3:7])[CH3:8]