Bromochloromethane → (3S)-1-chloro-3-(diphenylmethylene)amino-4-phenyl-2-butanone

HRID 2301732Notes

Reaction equation

C[O:2][C:3](=O)[C@H:4]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[N:5]=[C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:28][Cl:29].CCCCCC.C([Li])CCC.[Cl-].[NH4+]>O1CCCC1>[Cl:29][CH2:28][C:3](=[O:2])[C@@H:4]([N:5]=[C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: -78 °C

Procedure

N-(diphenylmethylene)-L-phenylalanine methyl ester (3.35 g) and bromochloromethane (0.83 ml) were added to dehydrated tetrahydrofuran (97 ml), and the mixture was cooled to −78° C. Then, a 1.53 M n-butyllithium hexane solution (8.3 ml) was added thereto. The mixture was stirred for 35 minutes. A saturated aqueous solution of ammonium chloride was added to the reaction solution to terminate the reaction. The resulting reaction solution was extracted twice with ethyl acetate at room temperature. The ethyl acetate layer was then washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After magnesium sulfate was removed, the ethyl acetate solution was concentrated to obtain desired (3S)-1-chloro-3-(diphenylmethylene)amino-4-phenyl-2-butanone (3.52 g) in a yield of 99.7%.

Workup

customto terminate
customthe reaction
customThe resulting reaction solution
extractionwas extracted twice with ethyl acetate at room temperature
washThe ethyl acetate layer was then washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
customAfter magnesium sulfate was removed
concentrationthe ethyl acetate solution was concentrated

Sources & evidence

ORD record: ord-9bf1ede13b524587936e6da71719234e
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500985B2

Reaction notes

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