Hydrochloric Acid → HCID 52914286, compound

HRID 2177671Notes

Reaction equation

HRID 2177671 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19]CC)=[O:18])=[C:15]([O:22][CH3:23])[C:14]([C:24]3[CH:28]=[CH:27][O:26][N:25]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Li+].O1CCOCC1.Cl>C(O)(C)C>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:22][CH3:23])[C:14]([C:24]3[CH:28]=[CH:27][O:26][N:25]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 67107596HCID 67107596, compound2×

Product 1

HCID 52914286HCID 52914286, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of ethyl 6-(benzenesulphonylmethyl)-3-(isoxazol-3-yl)-2-methoxybenzoate (Intermediate 47, 0.03 g), lithium hydroxide (1M aqueous solution, 0.4 ml) and dioxane (1 ml) was stirred at room temperature overnight then heated at 40° C. for 8 hours. It was left to stand at room temperature overnight then heated at 60° C. for 6 hours. The resultant mixture was acidified by addition of concentrated hydrochloric acid followed by addition of isopropanol (˜0.5 ml). The mixture was purified by preparative HPLC (C18), eluting with a mixture of methanol and water containing 0.1% formic acid with a gradient of 40-98% to give 6-(benzenesulphonylmethyl)-3-(isoxazol-3-yl)-2-methoxybenzoic acid (0.02 g) as a clear glass.

Workup

  1. temperaturethen heated at 40° C. for 8 hours
  2. waitIt was left
  3. waitto stand at room temperature overnight
  4. temperaturethen heated at 60° C. for 6 hours
  5. customThe mixture was purified by preparative HPLC (C18)
  6. washeluting with a mixture of methanol and water containing 0.1% formic acid with a gradient of 40-98%

Sources & evidence

ORD record
ord-95b4d42cd4564155a4ce642db107b8c7
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

Loading…