Acetyl chloride → HCID 18367397, compound

HRID 1741373Notes

Reaction equation

HRID 1741373 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH:22]([CH2:23][C:24]4[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=4)[O:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:21][CH2:20][NH:19]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.[C:35](Cl)(=[O:37])[CH3:36].[OH-].[Na+]>C1COCC1.O>[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH:22]([CH2:23][C:24]4[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=4)[O:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:21][CH2:20][N:19]3[C:35](=[O:37])[CH3:36])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 18367424HCID 18367424, compound

Product 1

HCID 18367397HCID 18367397, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-[[2-(4,5-diphenyloxazol-2-yl)pyrrolidin-3-yl]methyl]phenoxy]acetic acid (140 mg) in a mixture of THF (10 ml) and water (10 ml) was added acetyl chloride (1.0 ml) dropwise at 0° C. keeping pH 8-9 with 1N NaOH solution. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, 1N-HCl and brine. The dried solvent was evaporated in vacuo and the residue was purified by trituration with hexane to afford [3-[[2-(4,5-diphenyloxazol-2-yl)-1-acetylpyrrolidin-3-yl]methyl]phenoxy]acetic acid (150 mg). FABMS (m/z): 497 (M+ +1) IR (Nujol): 3400, 1600 cm-1NMR (DMSO-d6, δ): 1.8-2.4 (5H, m), 2.6-3.1 (3H, m), 3.2-3.9 (2H, m), 4.58, 4.61 (2H, each s), 4.8-5.2 (1H, m), 6.6-7.0 (3H, m), 7.1-7.8 (11H, m)

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water, 1N-HCl and brine
  3. customThe dried solvent was evaporated in vacuo
  4. customthe residue was purified by trituration with hexane

Sources & evidence

ORD record
ord-7aad529cdec940e1961ae93ee1bd1d79
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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