Sodium Hydroxide → HCID 9955802, compound

HRID 2305219Notes

Reaction equation

HRID 2305219 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[C@H:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=4)[C:28]([O:30]C)=[O:29])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C.O1CCCC1>[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[C@H:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=4)[C:28]([OH:30])=[O:29])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53740887HCID 53740887, compound

Product 1

HCID 9955802HCID 9955802, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (S)-3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoate (0.3 g) in a mixture of ethanol (8 ml) and tetrahydrofuran (5 ml) was added 1N-sodium hydroxide solution (3.5 ml). After stirring the mixture for 24 hours at the same temperature, the solvent was removed. The residue was partitioned between EtOAc and 1N-hydrochloric acid, and the organic layer was washed with brine. The dried solvent was evaporated in vacuo and the obtained solid was washed with a mixture hexane and ether to afford (S)-3-{[2-(4,5-diphenyl-oxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoic acid (0.28 g).

Workup

  1. customthe solvent was removed
  2. customThe residue was partitioned between EtOAc and 1N-hydrochloric acid
  3. washthe organic layer was washed with brine
  4. customThe dried solvent was evaporated in vacuo
  5. washthe obtained solid was washed with a mixture hexane and ether

Sources & evidence

ORD record
ord-90a3eba0a3174f428e0a81902060780c
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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