Methanol → 4-Amino-L-phenylalanine methyl ester

HRID 36126노트

반응식

HRID 36126 반응식
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:18]O>C(OCC)(=O)C>[CH3:18][O:10][C:9](=[O:11])[C@H:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:13][CH:12]=1)[NH2:8]

참가 물질

5

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1510014-Aminophenylalanine

생성물 1

HCID 206108304-Amino-L-phenylalanine methyl ester수율 88.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of p-aminophenylalanine (2.05 g, 9.9 mmol) in methanol (100 ml) at 0° C. was added thionyl chloride (20 ml) dropwise. Upon complete addition the reaction mixture was heated under reflux. After 24 hours the reaction mixture was cooled and reduced under pressure to give a brown oil. The brown oil was taken up in ethyl acetate (200 ml) and washed with saturated sodium bicarbonate solution (200 ml). The aqueous layer was further extracted with ethyl acetate (5×200 ml). The combined organic layer was dried over MgSO4 and reduced under pressure to yield the title compound as a brown solid (1.7 g, 88.5%).

후처리

  1. additionUpon complete addition the reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux
  4. temperatureAfter 24 hours the reaction mixture was cooled
  5. customto give a brown oil
  6. washwashed with saturated sodium bicarbonate solution (200 ml)
  7. extractionThe aqueous layer was further extracted with ethyl acetate (5×200 ml)
  8. dry with materialThe combined organic layer was dried over MgSO4

출처 및 근거

ORD 기록
ord-8532da8425fd4449b98d17aac0460488
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05412145

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