L-Phenylalanine → Benzyloxycarbonyl-L-phenylalanine

HRID 246888

반응식

HRID 246888 반응식
[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

참가 물질

5

반응물 2

HCID 6140L-PhenylalanineHCID 10387Benzyl chloroformate

생성물 1

HCID 70878Benzyloxycarbonyl-L-phenylalanine

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 14798Sodium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e6325b7d4f154ac89912391f7daa210c
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04704464

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