Hydrochloric Acid → (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propanoic acid

HRID 327790

반응식

HRID 327790 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:21]([OH:23])=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24]OS(OC)(=O)=O.Cl>[OH-].[Na+]>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:21]([OH:23])=[O:22])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:24])=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 6497Dimethyl Sulfate2회HCID 712438N-benzyloxycarbonyl-l-tyrosine

생성물 1

HCID 10496574(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propanoic acid수율 18%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

실험 절차

N-Benzyloxycarbonyl-L-tyrosine (31.5 g, 0.1 mol) was dissolved in aqueous sodium hydroxide (10 g in 100 ml H2O) and dimethylsulphate (10.5 ml, 0.11 mol) added dropwise to the stirred solution. The reaction was stirred overnight, additional dimethylsulphate (2 ml) added in one portion and the reaction stirred for a further 48 hours. 2M Hydrochloric acid was added until a white precipitate formed. This was filtered off, taken up in ethyl acetate, washed with brine and dried over anhydrous sodium sulphate, filtered and evaporated. The residue was crystallised from ethyl acetate to give N-benzyloxycarbonyl-O-methyl-L-tyrosine (5.8 g, 18%) as a white crystalline solid.

후처리

  1. stirringthe reaction stirred for a further 48 hours
  2. customformed
  3. filtrationThis was filtered off
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallised from ethyl acetate

출처 및 근거

ORD 기록
ord-b951a3694623411cb46884c0edc0c725
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05274094

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