Cyclopropylamine → Benzyl rac-alpha-[[[1-(cyclopropylcarbamoyl)-1-methylethyl]sulfonyl]methyl]hydrocinnamate

HRID 275598Notes

Reaction equation

HRID 275598 reaction equation
[CH2:1]([O:8][C:9]([CH:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:12][S:13]([C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18])(=[O:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:29]1([NH2:32])[CH2:31][CH2:30]1>N1C=CC=CC=1>[CH:29]1([NH:32][C:17]([C:16]([S:13]([CH2:12][CH:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])(=[O:15])=[O:14])([CH3:21])[CH3:20])=[O:18])[CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 20088482(RS)-2-[[2-[(Benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride

Product 1

HCID 67807703Benzyl rac-alpha-[[[1-(cyclopropylcarbamoyl)-1-methylethyl]sulfonyl]methyl]hydrocinnamateYield 86.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1.07 g (2.5 mmol) of (RS)-2-[[2-[(benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride and 0.42 g (7.4 mmol) of cyclopropylamine in 20 ml of pyridine was stirred at room temperature for 2 hours. Thereafter, the reaction solution was evaporated under reduced pressure and the residue was chromatographed on 30 g of silica gel using a 99:1 mixture of methylene chloride and methanol as the eluent. There was obtained 0.96 g of benzyl rac-α-[[[1-(cyclopropylcarbamoyl)-1-methylethyl]sulfonyl]methyl]hydrocinnamate as a yellowish solid, MS: 444 (M)+.

Workup

  1. customThereafter, the reaction solution was evaporated under reduced pressure
  2. customthe residue was chromatographed on 30 g of silica gel using
  3. additiona 99:1 mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-889cd3b891e742e8869cfd313c6de001
Source dataset
uspto-grants-1995_02
Patent number
US05393875

Reaction notes

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