Lithium Hydroxide → HCID 67168497, compound

HRID 872674Notes

Reaction equation

HRID 872674 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[O:12][CH:13]=[C:14]([C:16]([O:18]CC)=[O:17])[N:15]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[OH-].[Li+]>C1COCC1.CO.O>[CH3:1][S:2]([N:5]1[CH2:6][CH2:7][CH:8]([C:11]2[O:12][CH:13]=[C:14]([C:16]([OH:18])=[O:17])[N:15]=2)[CH2:9][CH2:10]1)(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67169151HCID 67169151, compound

Product 1

HCID 67168497HCID 67168497, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ethyl 2-(1-(methylsulfonyl)piperidin-4-yl)oxazole-4-carboxylate (590 mg, 1.951 mmol) was dissolved in THF/methanol mixture (9:1) and 1M lithium hydroxide (3.90 ml, 3.90 mmol) was added slowly. The reaction mixture was stirred at RT for 1 h, diluted with water and pH was adjusted to 1.5. The mixture was extracted three times with ethyl acetate. Ethyl acetate phases were combined and evaporated to yield the title compound (74.7%). 1H-NMR (400 MHz; DMSO): δ 1.68-1.81 (m, 2H), 2.06-2.15 (m, 2H), 2.85-2.96 (m, 5H), 2.99-3.10 (m, 1H), 3.51-3.59 (m, 2H), 8.67 (s, 1H), 13.02 (bs, 1H).

Workup

  1. extractionThe mixture was extracted three times with ethyl acetate
  2. customevaporated

Sources & evidence

ORD record
ord-013e061500ce40a6aadddfec868725af
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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