N-bromobutanimide → 2-(Tert-butoxycarbonylamino)-4-bromomethylthiazole-5-carboxylic acid benzylamide

HRID 45397Notes

Reaction equation

HRID 45397 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N:13][C:12]=1[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:25]N1C(=O)CCC1=O>C(#N)C>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])=[N:13][C:12]=1[CH2:24][Br:25])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 866425212-(Tert-butoxycarbonylamino)-4-methylthiazole-5-carboxylic acid benzylamide

Product 1

HCID 866425222-(Tert-butoxycarbonylamino)-4-bromomethylthiazole-5-carboxylic acid benzylamideYield 58.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)-4-methylthiazole-5-carboxylic acid benzylamide (0.108 g, 0.31 mmol) in acetonitrile (10 mL) was added N-bromosuccinimide (0.071 g, 0.40 mmol). The resultant mixture was stirred at ambient temperature until the reaction was completed. The reaction mixture was concentrated in vacuo and the crude product was purified by flash column chromatography eluting with ethyl acetate/hexanes (5/95 to 100/0) to afford 2-(tert-butoxycarbonylamino)-4-bromomethylthiazole-5-carboxylic acid benzylamide (0.077 g, 58% yield).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude product was purified by flash column chromatography
  3. washeluting with ethyl acetate/hexanes (5/95 to 100/0)

Sources & evidence

ORD record
ord-ee454d777a8341a7b1a9b79216a7a26c
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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