HRID1840617

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

HCID25134

Boron tribromide

BBr3

结构：COc1cc(CN2C(=O)N([C@@H](CC3CC3)C(=O)N[C@H](C)CC(=O)O)C(=O)C2(C)C)ccc1NC(=O)Nc1ccccc1C

HCID9960205

未命名化合物

PRODUCTS

生成物

结构：Cc1ccccc1NC(=O)Nc1ccc(CN2C(=O)N([C@@H](CC3CC3)C(=O)N[C@H](C)CC(=O)O)C(=O)C2(C)C)cc1O

HCID12044588

未命名化合物

收率 36%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

CONDITIONS

反应条件

温度: 0 °C

PROCEDURE

实验过程

211 μL of boron tribromide were added under argon to a solution of 100 mg (0.169 mmol) of the compound of Example 1 in 20 mL of absolute dichloromethane at −78° C. and the reaction mixture was allowed to warm to 0° C. with ice cooling. After 30 minutes at 0° C., water was cautiously added. The phases were separated and the organic phase was dried over sodium sulfate. After filtration, removal of the solvent in vacuo, chromatographic purification by preparative HPLC and freeze drying of the product fractions, 35 mg (36%) of the title compound were obtained.

WORKUP

后处理

customThe phases were separated
dry with materialthe organic phase was dried over sodium sulfate
filtrationAfter filtration, removal of the solvent
customin vacuo, chromatographic purification by preparative HPLC
customfreeze drying of the product fractions

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-8b39a3518e634d4690251a19d79510a3
来源数据集: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06680333B2
来源说明: uspto-grants-2004_01

反应 SMILES

B(Br)(Br)Br.[CH3:5][C:6]1([CH3:47])[C:10](=[O:11])[N:9]([C@@H:12]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[C:13]([NH:15][C@H:16]([CH3:21])[CH2:17][C:18]([OH:20])=[O:19])=[O:14])[C:8](=[O:26])[N:7]1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[CH3:44])=[O:36])=[C:30]([O:45]C)[CH:29]=1.O>ClCCl>[CH3:47][C:6]1([CH3:5])[C:10](=[O:11])[N:9]([C@@H:12]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[C:13]([NH:15][C@H:16]([CH3:21])[CH2:17][C:18]([OH:20])=[O:19])=[O:14])[C:8](=[O:26])[N:7]1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[CH3:44])=[O:36])=[C:30]([OH:45])[CH:29]=1