Methanol → 2-Cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acid

HRID 987232Notes

Reaction equation

HRID 987232 reaction equation
C([O:3][C:4](=[O:29])[CH:5]([C:27]#[N:28])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)C.O.[OH-].[Li+].CO>O.O1CCCC1>[C:27]([CH:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=2)=[CH:11][CH:12]=1)[C:4]([OH:29])=[O:3])#[N:28]

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 179303192-Cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester

Product 1

HCID 229887662-Cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acidYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester (described in Example 7) (0.9 g; 2.16 mmole), lithium hydroxide hydrate (0.12 g; 2.86 mmole), methanol (5 ml), water (5 ml) and tetrahydrofuran (10 ml) was stirred for 30 minutes at room temperature. Water was added and the mixture was washed with diethyl ether. The water phase was acidified with hydrochloric acid and extracted with ethyl acetate. The organic phase was dried (sodium sulfate), filtered and evaporated in vacuo. The crude product was purified by crystallization in diisopropyl ether to give 0.56 g (yield 67%) of 2-cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acid.

Workup

  1. washthe mixture was washed with diethyl ether
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude product was purified by crystallization in diisopropyl ether

Sources & evidence

ORD record
ord-96cf840335fc4caa8282c2bca2a0d055
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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