HRID2297053

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID69858

2,3,5,6-Tetrafluorophenol

C6H2F4O

HCID522689

Potassium fluoride

结构：CC(C)Cc1c(C(=O)N[C@H](C(=O)NC(CC(=O)OC(C)(C)C)C(=O)CBr)C(C)C)n(C)c2ccccc12

HCID86756359

未命名化合物

PRODUCTS

生成物

结构：CC(C)Cc1c(C(=O)N[C@H](C(=O)NC(CC(=O)OC(C)(C)C)C(=O)COc2c(F)c(F)cc(F)c2F)C(C)C)n(C)c2ccccc12

HCID86756358

未命名化合物

结构：CC(C)Cc1c(C(=O)N[C@H](C(=O)C(C(=O)OC(C)(C)C)C(N)C(=O)COc2c(F)c(F)cc(F)c2F)C(C)C)n(C)c2ccccc12

HCID131723666

未命名化合物

收率 44%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

Potassium fluoride (21.6 mg, 0.37 mmol) was added to a solution of N-[(1-methyl-3-isobutyl-indole-2-cabonyl)valinyl]-3-amino-5-bromo-4-oxo-pentanoic acid, tert-butyl ester (86.1 mg, 0.149 mmol) and 2,3,5, 6-tetrafluorophenol (27.0 mg, 0.163 mmol in DMF (2.0 ml). After stirring at room temperature for 3 hours, the reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was back-extracted with ethyl acetate. The organic layers were combined, washed with saturated NaHCO3 solution, and brine, dried over sodium sulfate, and concentrated. The residue was triturated with ether to give the titled product, N-(1-methyl-3-isobutyl-indole-2-cabonyl)-valinyl-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester as a white solid (43.8 mg, 44%). TLC (hexane/EtOAc, 50/50): Rf=0.50.

WORKUP

后处理

customthe reaction mixture was partitioned between ethyl acetate and water
extractionThe aqueous layer was back-extracted with ethyl acetate
washwashed with saturated NaHCO3 solution, and brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was triturated with ether

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-b8a4c2d1154744018ded014a58ca1e72
来源数据集: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06489353B2
来源说明: uspto-grants-2002_12

反应 SMILES

[F-].[K+].[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][CH:14]([CH3:16])[CH3:15])=[C:5]1[C:17]([NH:19][C@H:20]([C:24]([NH:26][CH:27]([C:36](=[O:39])[CH2:37]Br)[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:25])[CH:21]([CH3:23])[CH3:22])=[O:18].[F:40][C:41]1[C:46]([F:47])=[CH:45][C:44]([F:48])=[C:43]([F:49])[C:42]=1[OH:50]>CN(C=O)C>[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][CH:14]([CH3:16])[CH3:15])=[C:5]1[C:17]([NH:19][C@H:20]([C:24]([NH:26][CH:27]([C:36](=[O:39])[CH2:37][O:50][C:42]1[C:43]([F:49])=[C:44]([F:48])[CH:45]=[C:46]([F:47])[C:41]=1[F:40])[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:25])[CH:21]([CH3:23])[CH3:22])=[O:18].[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][CH:14]([CH3:16])[CH3:15])=[C:5]1[C:17]([NH:19][C@H:20]([C:24]([CH:28]([CH:27]([NH2:26])[C:36](=[O:39])[CH2:37][O:50][C:42]1[C:41]([F:40])=[C:46]([F:47])[CH:45]=[C:44]([F:48])[C:43]=1[F:49])[C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])=[O:25])[CH:21]([CH3:22])[CH3:23])=[O:18]