N-[4-(2-Bromoacetyl)Phenyl]Acetamide → (R)-1-[2-(4-acetylamino-phenyl)-2-oxo-ethyl]-3-((R)-2-phenyl-2-phenylamino-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 77037

반응식

HRID 77037 반응식
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:25])[C@@H:11]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:2]2.[Br:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:39])[CH3:38])=[CH:32][CH:31]=1)=[O:29]>C(#N)C>[Br-:26].[C:37]([NH:36][C:33]1[CH:34]=[CH:35][C:30]([C:28](=[O:29])[CH2:27][N+:1]23[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]2)[C@@H:3]([O:9][C:10](=[O:25])[C@@H:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:2]3)=[CH:31][CH:32]=1)(=[O:39])[CH3:38]

참가 물질

4

반응물 2

HCID 12364739N-[4-(2-Bromoacetyl)Phenyl]AcetamideHCID 46840261(R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate

생성물 1

HCID 86643225(R)-1-[2-(4-acetylamino-phenyl)-2-oxo-ethyl]-3-((R)-2-phenyl-2-phenylamino-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture (R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (Diastereoisomer 1 of C2) (80.0 mg, 0.24 mmol) and N-(4-(2-bromoacetyl)phenyl)acetamide (60.9 mg, 0.24 mmol) in acetonitrile (2 mL) is heated in a microwave oven at 100° C. for 1 hour (UPLC-MS monitoring: complete conversion). The title compound is isolated by suction filtration and washed with Et2O (98.2 mg, 81% yield, off-white solid, bromide salt, single diastereoisomers).

출처 및 근거

ORD 기록
ord-7393a6051a614150bb46293b09cf5475
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835682B2

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