Hydrochloric Acid → HCID 68278120, compound

HRID 931501Notes

Reaction equation

HRID 931501 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1)(=[O:20])=[O:19].[ClH:34]>>[ClH:34].[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1)(=[O:19])=[O:20]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 68277912HCID 68277912, compound

Product 1

HCID 68278120HCID 68278120, compoundYield 68%

Procedure

A solution of methyl 4-(5-methyl-4-((4-(piperidin-1-ylmethyl)phenylsulfonyl)methyl)oxazol-2-yl)benzoate (2 g, 2.65 mmol, 1.00 equiv, 62%) in 6N hydrochloric acid (50 mL) was refluxed overnight. The resulting mixture was concentrated under vacuum and the residue was washed with 20 mL of ethyl acetate and 20 mL of ether. The solid was dried in a vacuum oven to give 1.2 g (68%) of 4-(5-methyl-4-((4-(piperidin-1-ylmethyl)phenylsulfonyl)methyl)oxazol-2-yl)benzoic acid hydrochloride as an off-white solid. LC-MS: (ES, m/z): 496 [M+CH3CN+H]+, 455 [M+H]+

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. washthe residue was washed with 20 mL of ethyl acetate and 20 mL of ether
  3. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-5a0d68b96cd74bafb7e187c71ef6d39c
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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