Hydrochloric Acid → HCID 67468592, compound

HRID 1519243Notes

Reaction equation

HRID 1519243 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[N:13]=[C:14]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[O:15][C:16]=2[S:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=2)=[CH:6][CH:5]=1.[Li+].[OH-].Cl>CO.C1COCC1.O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([S:17][C:16]2[O:15][C:14]([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)=[N:13][C:12]=2[CH2:11][O:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:32])=[O:2])=[CH:9][CH:8]=2)=[N:19][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71184062HCID 71184062, compound

Product 1

HCID 67468592HCID 67468592, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of Methyl-4-({5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methoxy)benzoate (0.31 g, 0.66 mmol) in 6 ml of 1:1 MeOH/THF was added 1N LiOH (1.98 ml, 1.98 mmol). The reaction was allowed to proceed at 55° C. for 2 h, at which point it was cooled to room temperature and was acidified by 3N HCl. The reaction mixture was diluted with water and extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to yield 4-({5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methoxy)benzoic acid as a white solid. It was used as is for the next step. LCMS [M+H]=457.3.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-af35ea163ca142bea981da9e5a6b51fc
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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