Benzyl Bromide → Benzyl 2-(1-(tert-butoxycarbonylamino)ethyl)thiazole-5-carboxylate

HRID 588503노트

반응식

HRID 588503 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[S:12][C:13]([C:16]([OH:18])=[O:17])=[CH:14][N:15]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CS(C)=O>[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[S:12][C:13]([C:16]([O:18][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:17])=[CH:14][N:15]=1)[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 14797Potassium Hydroxide2회HCID 673960092-(1-{[(Tert-butoxy)carbonyl]amino}ethyl)-1,3-thiazole-5-carboxylic acid

생성물 1

HCID 67395421Benzyl 2-(1-(tert-butoxycarbonylamino)ethyl)thiazole-5-carboxylate수율 73.4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of 2-(1-(tert-butoxycarbonylamino)ethyl)thiazole-5-carboxylic acid (0.14 g, 0.5 mmol) in DMSO (1 mL) was added KOH (0.031 g, 0.55 mmol). The mixture was stirred at room temperature until the full dissolution of KOH was observed. Benzyl bromide (0.06 mL, 0.53 mmol) was added and the reaction solution was stirred at room temperature overnight. The solution was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was dried over anhydrous MgSO4, concentrated and purified by column chromatography to afford a colorless oil (0.133 g, 73%). LC-MS: (FA) ES+ 363.

후처리

  1. customThe solution was partitioned between EtOAc and saturated aqueous NaHCO3
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. concentrationconcentrated
  4. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-0e5263224ad345e485367e974c964a6a
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227951B2

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