Diisopropylethylamine → Benzyl 4-({2-[(tert-butoxycarbonyl)amino]ethyl}[(4-chlorophenyl)methyl]carbamoyl)piperazine-1-carboxylate

HRID 388291

Reaction equation

HRID 388291 reaction equation
Cl[C:2]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1)=[O:3].[Cl:20][C:21]1[CH:38]=[CH:37][C:24]([CH2:25][NH:26][CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C>ClCCl>[C:32]([O:31][C:30]([NH:29][CH2:28][CH2:27][N:26]([CH2:25][C:24]1[CH:37]=[CH:38][C:21]([Cl:20])=[CH:22][CH:23]=1)[C:2]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1)=[O:3])=[O:36])([CH3:35])([CH3:33])[CH3:34]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 193585684-Cbz-piperazine-1-carbonyl ChlorideHCID 67134877HCID 67134877, compound

Product 1

HCID 53416583Benzyl 4-({2-[(tert-butoxycarbonyl)amino]ethyl}[(4-chlorophenyl)methyl]carbamoyl)piperazine-1-carboxylateYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl 4-(chlorocarbonyl)piperazine-1-carboxylate (233 mg, 0.83 mmol) was added at room temperature to a solution of tert-butyl 2-(4-chlorobenzylamino)ethylcarbamate (235 mg, 0.83 mmol) and Hunig's base (0.2 mL, 1.2 mmol, 1.5 eq.) in dichloromethane (1.6 mL). The reaction was allowed to stir overnight. The reaction mixture was then concentrated to the crude product, which was purified by flash column chromatography to afford benzyl 4-((2-(tert-butoxycarbonylamino)ethyl)(4-chlorobenzyl)carbamoyl)piperazine-1-carboxylate as foam (167 mg, 38%). MS (ESI) m/e (M+H+) 531.

Workup

  1. concentrationThe reaction mixture was then concentrated to the crude product, which
  2. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-10ff3e579a4041e7909d63735ab85d82
Source dataset
uspto-grants-2013_02
Patent number
US08377937B2

Linked notes

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