Sulfuric Acid → HCID 69025192, compound

HRID 2113155Notes

Reaction equation

HRID 2113155 reaction equation
[CH2:1]([C@:3]([OH:18])([C@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>[Pd].C(O)(=O)C>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:9][C@@:3]([OH:18])([CH2:1][CH3:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 69024381HCID 69024381, compound

Product 1

HCID 69025192HCID 69025192, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Ethyl (2S, 3S)-2-ethyl-3-(2-fluorophenyl)-2,3-dihydroxypropanoate (5.2 g, 20 mmol), 10% palladium on carbon (2.5 g) and concentrated sulfuric acid (0. 53 mL, 10 mmol) were mixed in acetic acid (100 mL). The reaction mixture was hydrogenated at 45 psi for 48 hrs. Sodium acetate (1.7 g, 20 mmol) was added and the reaction mixture was stirred for 10 min before it was filtered through silica gel. Concentration of the filtrate gave essentially pure ethyl (2S)-2-(2-Fluoro-benzyl)-2-hydroxy-butyrate, which was hydrolyzed with KOH (2 N, 25 mL) in methanol (150 mL) to give the title compound.

Workup

  1. filtrationwas filtered through silica gel

Sources & evidence

ORD record
ord-e38fe50aa70b45dc9f3c89ea7ded7789
Source dataset
uspto-grants-2009_04
Patent number
US07524882B2

Reaction notes

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