HRID40008

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID887

Methanol

CH4O

HCID14798

Sodium Hydroxide

HNaO

2 次

结构：COC(=O)C1CC(N(Cc2ccc(C)c(F)c2)C(=O)OC(C)(C)C)CCN1CCn1c(=O)cnc2ccc(OC)cc21

HCID59397959

未命名化合物

PRODUCTS

生成物

结构：COc1ccc2ncc(=O)n(CCN3CCC(N(Cc4ccc(C)c(F)c4)C(=O)OC(C)(C)C)CC3C(=O)O)c2c1

HCID59398421

未命名化合物

收率 39.7%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

PROCEDURE

实验过程

To 5 mL of a methanol solution containing 80 mg of methyl 4-((tert-butoxycarbonyl) (3-fluoro-4-methybenzyl)amino)-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylate, 0.2 mL of 2 mol/L aqueous sodium hydroxide solution was added at room temperature, and stirred for 2.5 hours. Further, 0.2 mL of 2 mol/L aqueous sodium hydroxide solution and 0.5 mL of water were added, stirred at the sane temperature for 4 hour and 40 min, and allowed to stand overnight. The solvent was removed under reduced pressure, and the reaction mixture was adjusted to pH 7.0 with 2 mol/L hydrochloric acid. To the mixture, water and ethyl acetate were added, the organic layer was separated, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 31 mg of 4-((tert-butoxycarbonyl) (3-fluoro-4-methybenzyl)amino)-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylic acid as a yellow solid. (2) To 5 mL of an ethyl acetate solution containing 31 mg of 4-((tert-butoxycarbonyl)(3-fluoro-4-methybenzyl)amino)-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylic acid, 0.1 mL of 4 mol/L hydrogen chloride/ethyl acetate solution was added at room temperature, and stirred for 6 hours and 40 min, further, 0.1 mL of 4 mol/L hydrogen chloride/ethyl acetate solution was added, and stirred for 3.5 hours. The resulting solid was filtered to give 30 mg of 4-((3-fluoro-4-methybenzyl)amino)-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylic acid hydrochloride as a yellow solid.

WORKUP

后处理

additionwas added at room temperature
stirringstirred at the sane temperature for 4 hour and 40 min
waitto stand overnight
customThe solvent was removed under reduced pressure
additionTo the mixture, water and ethyl acetate were added
customthe organic layer was separated
washwashed with aqueous saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-bd918e80af37435f9a7a658f6a6b39ef
来源数据集: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08524738B2
来源说明: uspto-grants-2013_09

反应 SMILES

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