L-Phenylalanine → Benzyloxycarbonyl-L-phenylalanine

HRID 246888

反応式

HRID 246888 の反応式
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>[OH-].[Na+].C(Cl)(Cl)Cl>[CH2:17]([O:16][C:14]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 2

HCID 6140L-PhenylalanineHCID 10387Benzyl chloroformate

生成物 1

HCID 70878Benzyloxycarbonyl-L-phenylalanine

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

100 mmoles (16.51 grams) of (L)-phenylalanine were dissolved in 50 ml of 2N NaOH, cooled in an ice bath and treated dropwise with 106 mmoles (15.04 ml) of benzyl chloroformate. Stirring at room temperature was carried out for 30 minutes. If the product precipitates out already, sufficient water is added thereto until a clear solution is attained. 4N Hydrochloric acid is dropped in until acid reaction (pH4) and shaken three times with ethyl acetate. The organic phases were dried over sodium sulfate and freed from solvent in a vacuum. There was obtained a colorless, oily product. It was dissolved in 200 ml of chloroform, precipitated in the cold by addition of 400 ml of petroleum ether and filtered off with suction in a large suction filter. Colorless crystals.

後処理

  1. temperaturecooled in an ice bath
  2. customIf the product precipitates out already
  3. additionsufficient water is added
  4. addition4N Hydrochloric acid is dropped in until acid reaction (pH4)
  5. stirringshaken three times with ethyl acetate
  6. dry with materialThe organic phases were dried over sodium sulfate
  7. customThere was obtained a colorless, oily product
  8. customprecipitated in the
  9. additioncold by addition of 400 ml of petroleum ether
  10. filtrationfiltered off with suction in a large suction
  11. filtrationfilter

出典と根拠

ORDレコード
ord-e6325b7d4f154ac89912391f7daa210c
出典データセット
uspto-grants-1987_11
特許番号
US04704464

関連ノート

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