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

HRID 466841ノート

反応式

HRID 466841 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cd95ac414ddb42fdaaf2a55809c7acef
出典データセット
uspto-grants-1992_10
特許番号
US05157041

反応ノート

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