N-BOC-ethylenediamine → t-Butyl [2-(2-bromo-5-phenyl-4-thiazolecarboxamido)ethyl]carbamate

HRID 1590887Notes

Reaction equation

HRID 1590887 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([C:7]([O:9]C)=O)[N:6]=1.[NH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24].NC1SC(C2C=CC=CC=2)=C(C(OC)=O)N=1>>[Br:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([C:7]([NH:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:9])[N:6]=1

Participants

4

Reactant 3

HCID 187201N-BOC-ethylenediamineHCID 664327Methyl 2-amino-5-phenyl-1,3-thiazole-4-carboxylateHCID 9814750Methyl 2-bromo-5-phenyl-1,3-thiazole-4-carboxylate

Product 1

HCID 54063106t-Butyl [2-(2-bromo-5-phenyl-4-thiazolecarboxamido)ethyl]carbamateYield 26%

Procedure

2.0 g (6.7 mmol) of methyl 2-bromo-5-phenyl-4-thiazolecarboxylate and 1.61 g (10.1 mmol) of t-butyl (2-aminoethyl)carbamate were stirred under reduced pressure for 2.5 hours at 110° bath temperature, whereby the methanol formed was distilled off continuously. After chromatography on 100 g of silica gel with methylene chloride and a 4:1 mixture of methylene chloride and ethyl acetate there was obtained 0.58 g (26%) of t-butyl [2-(2-bromo-5-phenyl-4-thiazolecarboxamido)ethyl]carbamate as a pale yellow, crystallizing oil which was used directly.

Workup

  1. customformed
  2. distillationwas distilled off continuously
  3. additionAfter chromatography on 100 g of silica gel with methylene chloride and a 4:1 mixture of methylene chloride

Sources & evidence

ORD record
ord-f62c51aa16834642968a998af1cf5702
Source dataset
uspto-grants-1993_04
Patent number
US05204482

Reaction notes

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