1-Hydroxybenzotriazole → Tert-butyl 4-({[2-(acetylamino)-1,3-thiazol-4-yl]carbonyl)amino}phenylcarbamate

HRID 1246440Notes

Reaction equation

HRID 1246440 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]([OH:12])=O)[N:9]=1)(=[O:3])[CH3:2].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:16][CH:15]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>ClCCl>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[CH:18][CH:19]=2)=[O:12])[N:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 688611tert-Butyl (4-aminophenyl)carbamateHCID 8401132-Acetamido-1,3-thiazole-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 21915112Tert-butyl 4-({[2-(acetylamino)-1,3-thiazol-4-yl]carbonyl)amino}phenylcarbamateYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(acetylamino)-1,3-thiazole-4-carboxylic acid (500 mg), tert-butyl 4-aminophenylcarbamate (615 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (566 mg), 1-hydroxybenzotriazole (399 mg) and dichloromethane (5 ml) was stirred at ambient temperature for 3 hours. The reaction mixture was washed with saturated aqueous sodium hydrogen bicarbonate, and the organic layer was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with 3% methanol/chloroform as an eluent. The crystalline residue was collected and washed with ethyl acetate to give tert-butyl 4-({[2-(acetylamino)-1,3-thiazol-4-yl]carbonyl}amino)phenylcarbamate (580 mg).

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium hydrogen bicarbonate
  2. concentrationthe organic layer was concentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel with 3% methanol/chloroform as an eluent
  4. customThe crystalline residue was collected
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-36a4f2abe82649478f24b03646f43cb2
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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