Hydrochloric Acid → Droxidopa

HRID 343999

반응식

HRID 343999 반응식
C([O:8][C:9]1[CH:10]=[C:11]([C@H:23]2[O:27]C(C3C=CC=CC=3)=[N:25][C@@H:24]2[C:34]([O:36]C)=[O:35])[CH:12]=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1.Cl>>[CH:12]1[C:11]([C@@H:23]([OH:27])[C@H:24]([NH2:25])[C:34]([OH:36])=[O:35])=[CH:10][C:9]([OH:8])=[C:14]([OH:15])[CH:13]=1

참가 물질

3

반응물 2

HCID 313Hydrochloric AcidHCID 56982455methyl (4S,5R)-5-(3,4-dibenzyloxyphenyl)-2-phenyl-2-oxazoline-4-carboxylate

생성물 1

HCID 92974Droxidopa수율 72%

실험 절차

Methyl (4S,5R)-5-(3,4-dibenzyloxyphenyl)-2-phenyl-2-oxazoline-4-carboxylate (157 mg, 0.50 mmol), was added to 1N-hydrochloric acid (5 ml) with stirring, and the mixture was refluxed for 17 hours. After cooling to room temperature, the reaction mixture was washed with ether and neutralized with 1N sodium hydroxide to obtain precipitated crystals. The precipitated crystal then was filtered to obtain 76 mg (0.36 mmol, yield: 71%) of L-threo DOPS.

후처리

  1. temperaturethe mixture was refluxed for 17 hours
  2. washthe reaction mixture was washed with ether and neutralized with 1N sodium hydroxide
  3. customto obtain
  4. customprecipitated crystals
  5. filtrationThe precipitated crystal then was filtered

출처 및 근거

ORD 기록
ord-e7486e55e15b4c2399f22201143c07e7
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05864041

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