Sodium Hydroxide → HCID 68277962, compound

HRID 931474Notes

Reaction equation

HRID 931474 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]([CH3:33])=[C:14]([CH2:16][S:17]([CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)(=[O:19])=[O:18])[N:15]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>C(O)C>[C:29]([O:28][C:26]([N:23]1[CH2:22][CH2:21][CH:20]([S:17]([CH2:16][C:14]2[N:15]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=3)[O:12][C:13]=2[CH3:33])(=[O:18])=[O:19])[CH2:25][CH2:24]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68278607HCID 68278607, compound

Product 1

HCID 68277962HCID 68277962, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 4-((2-(4-(methoxycarbonyl)phenyl)-5-methyloxazol-4-yl)methylsulfonyl)piperidine-1-carboxylate (980 mg, 2.05 mmol, 1.00 equiv), sodium hydroxide (120 mg, 3.00 mmol, 1.50 equiv) in ethanol (10 mL) was stirred at 50° C. overnight in a 100-mL round-bottom flask. The reaction mixture was concentrated under vacuum and quenched by the addition of 30 mL of water/ice. The pH value of the solution was adjusted to 3 with the addition of 3M hydrochloric acid. The precipitate was collected by filtration and dried to give 0.76 g (80%) of 4-(4-((1-(tert-butoxycarbonyl)piperidin-4-ylsulfonyl)methyl)-5-methyloxazol-2-yl)benzoic acid as a white solid. LC-MS: (ES, m/z): 409 [M-C4H9+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customquenched by the addition of 30 mL of water/ice
  3. additionThe pH value of the solution was adjusted to 3 with the addition of 3M hydrochloric acid
  4. filtrationThe precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-c6708bc7163b408887e1dc0c23536056
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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