HCID 22012440, compound → HCID 22012474, compound

HRID 1533271Notes

Reaction equation

HRID 1533271 reaction equation
[OH:1][CH:2]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([O:24]C)=[O:23])=[CH:18][CH:17]=1)[CH:3]([C:7]1[CH:12]=[CH:11][C:10]2[O:13][CH2:14][O:15][C:9]=2[CH:8]=1)[C:4]([OH:6])=[O:5]>[OH-].[Na+].CO>[OH:1][CH:2]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=1)[CH:3]([C:7]1[CH:12]=[CH:11][C:10]2[O:13][CH2:14][O:15][C:9]=2[CH:8]=1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 22012440HCID 22012440, compound

Product 1

HCID 22012474HCID 22012474, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of (2RS,3SR)-3-hydroxy-2-(3,4-methylenedioxy-phenyl)-3-(4-methoxycarbonylphenyl)propionic acid (80 mg) in 1N aqueous sodium hydroxide solution (1.2 ml) and methanol (5 ml) was stirred at ambient temperature for 18 hours. The reaction was quenched with iN-hydrochloric acid and then the resulting mixture was diluted with ethyl acetate. The layers were separated and the organic layer was washed with brine. The organic layer was dried and evaporated to afford (2RS,3SR)-3-hydroxy-2-(3,4-methylenedioxyphenyl)-3-(4-carboxyphenyl)propionic acid (60 mg).

Workup

  1. customThe reaction was quenched with iN-hydrochloric acid
  2. additionthe resulting mixture was diluted with ethyl acetate
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. customThe organic layer was dried
  6. customevaporated

Sources & evidence

ORD record
ord-8a1d1d2c58ee4d2f9957e30449e90f2a
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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