Lithium Hydroxide → HCID 178484857, compound

HRID 25665Notes

Reaction equation

HRID 25665 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][CH2:5][O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]([CH3:27])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:9][CH2:8]1.[Li+].[OH-].OS([O-])(=O)=O.[K+]>C1COCC1>[CH3:27][N:13]([S:14]([C:17]1[CH:18]=[CH:19][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:21][CH:22]=1)(=[O:16])=[O:15])[C@H:10]1[CH2:11][CH2:12][C@H:7]([O:6][CH2:5][CH2:4][C:3]([OH:28])=[O:2])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 178500919HCID 178500919, compound

Product 1

HCID 178484857HCID 178484857, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.14 g (2.7 mmol) trans-3-{4-[Methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionic acid methyl ester in 27 ml THF were treated with 27 ml 1M LiOH for 1 h at RT. The was acidified by adding 1M KHSO4, and the mixture was extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4 and evaporated to give 1.1 g (quant.) trans-3-{4-[Methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionic acid as colorless oil, MS: 408 (M−H)−.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-eb149397390941fca0930530fc7bff5a
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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