Benzyl chloroformate → (3S)-3-Benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanone

HRID 413989Notes

Reaction equation

HRID 413989 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4](=[O:7])[CH2:5][Cl:6].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C(=O)([O-])O.[Na+]>O.C1(C)C=CC=CC=1>[CH2:19]([O:18][C:16]([NH:2][C@@H:3]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4](=[O:7])[CH2:5][Cl:6])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 56777393(S)-3-Amino-1-chloro-4-phenylbutan-2-one hydrochloride

Product 1

HCID 99625(3S)-3-Benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanoneYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

(3S)-3-Amino-1-chloro-4-phenyl-2-butanone hydrochloride (100 mg) was dissolved in water (4.3 ml). A solution (5.3 ml) of benzyl chloroformate (0.794 ml) in toluene was added to the obtained solution. Further, an aqueous solution (1.0 ml) of sodium hydrogencarbonate (71.9 mg) was added dropwise to the obtained mixture. They were stirred at room temperature for 50 minutes to conduct the reaction and then the aqueous layer was separated. The obtained toluene layer was analyzed by HPLC to find that (3S)-3-benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanone (118 mg) was obtained in a yield of 83%.

Workup

  1. customthe reaction
  2. customthe aqueous layer was separated
  3. customwas obtained in a yield of 83%

Sources & evidence

ORD record
ord-5c6d57d1703544d8b1b28c984328ce38
Source dataset
uspto-grants-2003_05
Patent number
US06570039B2

Reaction notes

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