Hydrochloric Acid → Droxidopa

HRID 343999Notes

Reaction equation

HRID 343999 reaction equation
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

Participants

3

Reactant 2

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

Product 1

HCID 92974DroxidopaYield 72%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e7486e55e15b4c2399f22201143c07e7
Source dataset
uspto-grants-1999_01
Patent number
US05864041

Reaction notes

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