Methanol → HCID 59576361, compound

HRID 2069518Notes

Reaction equation

HRID 2069518 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][C:6]1[N:7]=[C:8]([NH:12][C:13]([C:15]2[N:16]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[F:32])[CH:17]=[C:18]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH:19]=2)=[O:14])[S:9][C:10]=1[Cl:11])C.CO.O.[OH-].[Li+]>C1COCC1.O>[Cl:11][C:10]1[S:9][C:8]([NH:12][C:13]([C:15]2[N:16]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[F:32])[CH:17]=[C:18]([CH2:20][CH:21]([CH3:22])[CH3:23])[CH:19]=2)=[O:14])=[N:7][C:6]=1[CH2:5][C:4]([OH:33])=[O:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 25126862HCID 25126862, compound

Product 1

HCID 59576361HCID 59576361, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(5-Chloro-2-{[1-(2,4-difluoro-benzyl)-4-isobutyl-1H-pyrrole-2-carbonyl]-amino}-thiazol-4-yl)-acetic acid ethyl ester was taken in THF and methanol and to it lithium hydroxide monohydrate in water was added and stirred for 16-18 hrs. at room temperature. After completion of the reaction, the solvent was evaporated; the residue was diluted with water and was washed with diethyl ether. The aqueous layer was acidified with 1N HCl and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated the solvent to get the title compound (5-Chloro-2-{[1-(2,4-difluoro-benzyl)-4-isobutyl-1H-pyrrole-2-carbonyl]amino}-thiazol-4-yl)-acetic acid (E1).

Workup

  1. customat room temperature
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. additionthe residue was diluted with water
  5. washwas washed with diethyl ether
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated the solvent

Sources & evidence

ORD record
ord-295b3e28abc444bb80238adfb10e5000
Source dataset
uspto-grants-2012_10
Patent number
US08299115B2

Reaction notes

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