Lithium Hydroxide → HCID 56589687, compound

HRID 1889202Notes

Reaction equation

HRID 1889202 reaction equation
C[O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[S:15][C:14]([NH:16][C:17](=[O:40])[CH:18]([C:28]3[CH:33]=[CH:32][C:31]([S:34]([CH:37]4[CH2:39][CH2:38]4)(=[O:36])=[O:35])=[CH:30][CH:29]=3)[O:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])=[N:13][CH:12]=2)=[CH:6][CH:5]=1.[Li+].[OH-]>C1COCC1.CO>[CH:37]1([S:34]([C:31]2[CH:30]=[CH:29][C:28]([CH:18]([O:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])[C:17]([NH:16][C:14]3[S:15][C:11]([O:10][C:7]4[CH:6]=[CH:5][C:4]([C:3]([OH:41])=[O:2])=[CH:9][CH:8]=4)=[CH:12][N:13]=3)=[O:40])=[CH:33][CH:32]=2)(=[O:35])=[O:36])[CH2:38][CH2:39]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 56592434HCID 56592434, compound

Product 1

HCID 56589687HCID 56589687, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

4-{2-[2-(4-Cyclopropanesulfonyl-phenyl)-2-(2,4-difluoro-phenoxy)-acetylamino]thiazol-5-yloxy}-benzoic acid methyl ester (1.4 g, 2.33 mmol, obtained in example A74) was taken in THF: MeOH (1:1, 20 mL), to it was added aqueous solution of LiOH (0.34 g, 7.94 mmol in 10 mL water) and stirred for 1-4 h. After completion of the reaction, organic solvent was removed under reduced pressure. The aqueous layer was washed with diisopropyl ether then acidified with 1 N HCl to pH 2. The solid formed was filtered, washed with water, followed by washing with diisopropyl ether & dried under vacuum to get the title compound (1.17 g, 86%).

Workup

  1. customAfter completion of the reaction, organic solvent
  2. customwas removed under reduced pressure
  3. washThe aqueous layer was washed with diisopropyl ether
  4. customThe solid formed
  5. filtrationwas filtered
  6. washwashed with water
  7. washby washing with diisopropyl ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-3285287352e1424f89cd6af69ac263bf
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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