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

HRID 588503Notes

Reaction equation

HRID 588503 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0e5263224ad345e485367e974c964a6a
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

Loading…