Hydrochloric Acid → HCID 67452761, compound

HRID 1519224Notes

Reaction equation

HRID 1519224 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:21]([O:23]C)=[O:22])=[N:6][CH:7]=1.[Li+].[OH-].Cl>CO.C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)=[N:11][C:10]=2[C:21]([OH:23])=[O:22])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67452988HCID 67452988, compound

Product 1

HCID 67452761HCID 67452761, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazole-4-carboxylate (0.20 g, 0.55 mmol) in 6 ml of 1:1 MeOH/THF was added 1N LiOH (2.19 ml, 2.19 mmol). After 1 h at room temperature, the reaction 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 5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazole-4-carboxylic acid as a white solid (0.19 g). The acid was used without further purification. LCMS [M+H]=351.3. 1H NMR (400 MHz, CDCl3) δ 8.39 (d, J=3 Hz, 1H), 8.09 (dd, J=8.6, 5.5 Hz, 2H), 7.61 (dd, J=8.5, 3 Hz, 1H), 7.24 (d, J=8.6 Hz, 1H), 7.15 (dd, J=8.6, 8.6 Hz, 2H), 3.94 (s, 3H).

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-3cc407297a0f4724a432fd06e88b3701
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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