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

HRID 1841650노트

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HRID 1841650 반응식
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

참가 물질

6

반응물 4

HCID 6333BromochloromethaneHCID 25517Ammonium ChlorideHCID 11142452Rac-methyl-n-(diphenylmethylene)phenylalaninateHCID 178418244HCID 178418244, 화합물

생성물 1

HCID 11325911(3S)-1-chloro-3-(diphenylmethylene)amino-4-phenyl-2-butanone수율 99.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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%.

후처리

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

출처 및 근거

ORD 기록
ord-e6b52593bdb14cdb8ea5aadd9805cf78
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06683214B2

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