Lithium hydroxide, monohydrate → [4-(2-Thienylmethoxymethyl)-2-(2-methylphenyl)benzoyl]methionine

HRID 1532853Notes

Reaction equation

HRID 1532853 reaction equation
C1COCC1.CO.C[O:9][C:10](=[O:40])[C@H:11]([CH2:36][CH2:37][S:38][CH3:39])[NH:12][C:13](=[O:35])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][O:21][CH2:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[CH:16][C:15]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34].O.[OH-].[Li+]>O>[S:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[CH2:22][O:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([NH:12][C@H:11]([C:10]([OH:40])=[O:9])[CH2:36][CH2:37][S:38][CH3:39])=[O:35])=[C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[CH:16]=1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21899815MeOH tetrahydrofuranHCID 70224587[4-(2-Thienylmethoxymethyl)-2-(2-methylphenyl)benzoyl]methionine methyl ester

Product 1

HCID 59949455[4-(2-Thienylmethoxymethyl)-2-(2-methylphenyl)benzoyl]methionine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution in 1:1 THF-methanol of [4-(2-thienylmethoxymethyl)-2-(2-methylphenyl)benzoyl]methionine methyl ester, prepared as in Example 272C was added a solution of lithium hydroxide hydrate (40 mg, 0.95 mmol) in water (0.5 mL) and the reaction mixture was stirred for 3.5 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between ether and water. Aqueous 2N HCl (1 mL) was added to the aqueous phase. The aqueous phase was extracted with ethyl acetate. The ethyl acetate extract was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give [4-(2-thienylmethoxymethyl)-2-(2-methylphenyl)benzoyl]methionine. The acid was dissolved in acetonitrile (5 mL) and a solution of lithium hydroxide hydrate (18 mg, 0.43 mmol) in water (8 mL) was added. The mixture was concentrated and the residue was dissolved in water, frozen and lyophilized to give [4-(2-thienylmethoxymethyl)-2-(2-methylphenyl)benzoyl]methionine lithium salt (204 mg) as a light-yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between ether and water
  3. additionAqueous 2N HCl (1 mL) was added to the aqueous phase
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f07216f70d74e39864796ee5bdddeb0
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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