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

HRID 2301736Notes

Reaction equation

HRID 2301736 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].C1(C)C=CC=CC=1.Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].C(=O)([O-])O.[Na+]>O>[CH2:26]([O:25][C:23]([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:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 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 1

HCID 962WaterSolvent

Procedure

(3S)-3-amino-1-chloro-4-phenyl-2-butanone hydrochloride (100 mg) was dissolved in water (4.3 ml), and a toluene solution (5.3 ml) of benzyl chloroformate (0.794 ml) was added thereto. An aqueous solution (1.0 ml) of sodium hydrogencarbonate (71.9 mg) was further added dropwise thereto while being stirred. After the mixture was reacted at room temperature for 50 minutes while being stirred, the aqueous layer was separated. The resulting toluene layer was analyzed by HPLC, and it was identified that (3S)-3-benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanone (118 mg) was obtained in a yield of 83%.

Workup

  1. customAfter the mixture was reacted at room temperature for 50 minutes
  2. stirringwhile being stirred
  3. customthe aqueous layer was separated
  4. customwas obtained in a yield of 83%

Sources & evidence

ORD record
ord-058355c0606b49aaab13ab2d2af08b0b
Source dataset
uspto-grants-2002_12
Patent number
US06500985B2

Reaction notes

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