N-bromobutanimide → 2-Bromo-5-((tert-butoxycarbonyl)amino)thiazole-4-carboxylic acid

HRID 2089297Notes

Reaction equation

HRID 2089297 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][CH:12]=[N:11][C:10]=1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:24])C(=O)C1>C(Cl)Cl>[Br:24][C:12]1[S:13][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[C:10]([C:14]([OH:16])=[O:15])[N:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 581822035-(Boc-amino)-thiazole-4-carboxylic acid

Product 1

HCID 581821562-Bromo-5-((tert-butoxycarbonyl)amino)thiazole-4-carboxylic acidYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(tert-butoxycarbonylamino)thiazole-4-carboxylic acid (1.72 g, 10 mmol) in DCM (50 mL) was added in three portions NBS (1.95 g, 11 mmol); the reaction mixture was stirred at ambient temperature for 1 h. Reaction was concentrated in vacuo; resulted residue was purified by silica gel column chromatography (6:1 Pet-ether-EtOAc) to afford 2-bromo-5-(tert-butoxycarbonylamino)thiazole-4-carboxylic acid (1.75 g, 70%) as white solid: 1H-NMR (CDCl3, 500 MHz) δ (ppm): 13.65 (s, 1H), 10.03 (s, 1H), 1.49 (s, 9H). MS (ESI) m/z: 324 [M+H+]

Workup

  1. customReaction
  2. concentrationwas concentrated in vacuo
  3. customresulted residue was purified by silica gel column chromatography (6:1 Pet-ether-EtOAc)

Sources & evidence

ORD record
ord-638c6db38e05468385967e05df2fbd37
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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