Methanol → (S)-2-(2-(4-(3-(2,4-difluorophenyl)ureido)phenyl)thiazole-4-carboxamido)-3-methylbutanoic acid

HRID 75857Notes

Reaction equation

HRID 75857 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:34])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:19][CH:20]=[C:21]([C:23]([NH:25][C@@H:26]([CH:31]([CH3:33])[CH3:32])[C:27]([O:29]C)=[O:28])=[O:24])[N:22]=2)=[CH:14][CH:13]=1.CO.[Li+].[OH-]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:34])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:19][CH:20]=[C:21]([C:23]([NH:25][C@@H:26]([CH:31]([CH3:32])[CH3:33])[C:27]([OH:29])=[O:28])=[O:24])[N:22]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 67352417(S)-methyl 2-(2-(4-(3-(2,4-difluorophenyl)ureido)phenyl)thiazole-4-carboxamido)-3-methylbutanoate

Product 1

HCID 67354364(S)-2-(2-(4-(3-(2,4-difluorophenyl)ureido)phenyl)thiazole-4-carboxamido)-3-methylbutanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (S)-methyl 2-(2-(4-(3-(2,4-difluorophenyl)ureido)phenyl)thiazole-4-carboxamido)-3-methylbutanoate (100 mg, 0.204 mmol) in THF (4 mL)+MeOH (1 ml), 1 ml of 1N LiOH (42.99 mg, 1.024 mmol) was added at RT and stirred for 2-3 hr. After completion of reaction, THF was removed under reduced pressure. Obtained material was dissolved in water, acidified with 1N HCl and white solid precipitated out. It was filtered and dried.

Workup

  1. customwas removed under reduced pressure
  2. dissolutionObtained material was dissolved in water
  3. customprecipitated out
  4. filtrationIt was filtered
  5. customdried

Sources & evidence

ORD record
ord-1fbf55b980f44011868a5e3060d4bc64
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

Loading…