(3S)-3-Benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanone → Benzyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

HRID 54066노트

반응식

HRID 54066 반응식
[BH4-].[Na+].[CH2:3]([O:10][C:11]([NH:13][C@H:14]([C:22]([CH2:24][Cl:25])=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CO.C(Cl)(Cl)Cl>O1CCCC1>[CH2:3]([O:10][C:11]([NH:13][C@@H:14]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C@H:22]([OH:23])[CH2:24][Cl:25])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

5

반응물 3

HCID 99625(3S)-3-Benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanoneHCID 4311764Sodium borohydrideHCID 21584188Chloroform methanol

생성물 1

HCID 10860587Benzyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate수율 54.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3.5 g of sodium borohydride were added to an ice-cooled stirred solution of 21 g of [N-(benzyloxycarbonyl)-L-phenylalanyl]methyl chloride in 500 ml of aqueous tetrahydrofuran. Stirring was continued for 0.5 hour and the solvent was removed by evaporation. The residue was partitioned between dichloromethane and water and then carefully acidified with concentrated hydrochloric acid. After working-up the organic phase gave a white solid which ran as two spots; Rf 0.4 and 0.5 (5% methanol/chloroform). The solids were extracted with boiling hexane until all of the higher running component had been extracted. The combined n-hexane extracts were evaporated and the residue was re-extracted with boiling n-hexane to remove a small amount (0.5 g) of the lower running component. In this manner there were obtained 11.5 g of 3(S)-(benzyloxyformamido)-1-chloro-4-phenyl-2(S)-butanol of melting point 151°-153° C. (from ethyl acetate/n-hexane).

후처리

  1. temperaturecooled
  2. customthe solvent was removed by evaporation
  3. customThe residue was partitioned between dichloromethane and water
  4. customgave a white solid which
  5. extractionThe solids were extracted with boiling hexane until all of the
  6. extractionhad been extracted
  7. customThe combined n-hexane extracts were evaporated
  8. extractionthe residue was re-extracted with boiling n-hexane
  9. customto remove a small amount (0.5 g) of the

출처 및 근거

ORD 기록
ord-e51dcc607b8f4406800810cdfcbffee5
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620987

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