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

HRID 588503ノート

反応式

HRID 588503 の反応式
[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]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 14797Potassium Hydroxide2 回HCID 673960092-(1-{[(Tert-butoxy)carbonyl]amino}ethyl)-1,3-thiazole-5-carboxylic acid

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0e5263224ad345e485367e974c964a6a
出典データセット
uspto-grants-2016_01
特許番号
US09227951B2

反応ノート

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