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Ethanol → ethyl (2S)-2-amino-3-(3,4-dimethoxyphenyl)propanoate

HRID 903627
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HRID 903627 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8].OS(O)(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH2:28](O)[CH3:29]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][C@@H:7]([C:9]([O:11][CH2:28][CH3:29])=[O:10])[NH2:8])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 106329463,4-Dimethoxyphenylalanine, L-

생성물 1

HCID 10060820ethyl (2S)-2-amino-3-(3,4-dimethoxyphenyl)propanoate수율 51%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A 47 g (0.21 mole) portion of 3,4-dimethoxyphenylalanine in 450 ml of absolute ethanol was treated with 31 ml of concentrated H2SO4. The reaction mixture was refluxed for 5 hours and poured into 1.6 l. of H2O. The solution was basified with a solution of 61 g of K2CO3 in 200 ml of water. The basified solution was extracted with three 600 ml portions of ethyl acetate. The combined extracts were washed with 1.4 l. of water, dried over MgSO4 overnight and filtered. The filtrate was concentrated under reduced pressure to give 27 g (51%) of the desired product, a light yellow-brown viscous oil which crystallized upon refrigeration.

후처리

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. additionpoured into 1.6 l
  3. extractionThe basified solution was extracted with three 600 ml portions of ethyl acetate
  4. washThe combined extracts were washed with 1.4 l
  5. dry with materialof water, dried over MgSO4 overnight
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-bb0767e48761447486f2da9168ac4d83
출처 데이터셋
uspto-grants-1980_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04228303

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