dimethyl (2R)-2-methoxybutanedioate → (R)-methoxy-succinic acid

HRID 412417Notes

Reaction equation

HRID 412417 reaction equation
C[O:2][C:3](=[O:12])[C@H:4]([O:10][CH3:11])[CH2:5][C:6]([O:8]C)=[O:7]>Cl>[CH3:11][O:10][C@H:4]([CH2:5][C:6]([OH:8])=[O:7])[C:3]([OH:12])=[O:2]

Participants

3

Reactant 1

HCID 2192492dimethyl (2R)-2-methoxybutanedioate

Product 1

HCID 5325475(R)-methoxy-succinic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The above (R)-2-methoxysuccinic acid dimethyl ester was suspended in 2 N aqueous hydrochloric acid, and heated to reflux for 30 min to give a clear solution. Upon evaporation of solvent in vacuo a quantitative yield of 2(R)-methoxysuccinic acid was obtained as an oil. The oil was redissolved in acetic anhydride (120 mL) and heated to 110° C. for 2 hours. Solvent was removed by rotary evaporation to leave an oil. Ice cooled methanol (150 mL) was added, and the mixture was stirred for 3 hours at 0° C. followed by 16 hours at room temperature. The solvent was removed to leave (R)-2-methoxysuccinic acid 1-methyl ester.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 min
  3. customto give a clear solution

Sources & evidence

ORD record
ord-771c2f7b24f34ece9c8ac247c756d862
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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