Water → Methyl 2-[[(1,1'-biphenyl)-4-yl]sulfonyl]amino-4,5-epoxypentanoate

HRID 413366Notes

Reaction equation

HRID 413366 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][CH:11]([CH2:16][CH:17]=[CH2:18])[C:12]([O:14][CH3:15])=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1.O.ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][CH:11]([CH2:16][CH:17]2[O:34][CH2:18]2)[C:12]([O:14][CH3:15])=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 23508264Methyl 2-[[(1,1'-biphenyl)-4-yl]sulfonyl]amino-4-pentenoate

Product 1

HCID 23508251Methyl 2-[[(1,1'-biphenyl)-4-yl]sulfonyl]amino-4,5-epoxypentanoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent2×

Procedure

To a solution of methyl 2-[[(1,1′-biphenyl)-4-yl]sulfonyl]amino-4-pentenoate 16a (2.0 g, 5.8 mmol) in CH2Cl2 (15 mL), NaHCO3 (0.58 g, 7 mmol) and water (10 mL) at 0° C., is added slowly m-chloroperbenzoic acid (3.3 g, 11.6 mmol, 57-86%). The reaction mixture is stirred overnight. The resulting mixture is diluted with aqueous NaHCO3, and the mixture is extracted three times with CH2Cl2. The combined CH2Cl2 layers are washed with NaHCO3, brine, dried over MgSO4 and concentrated to an oil which is purified by column chromatography eluting with EtOAc/hexane (4:6) to give the desired product as a mixture of two isomers (ratio 2:3).

Workup

  1. extractionthe mixture is extracted three times with CH2Cl2
  2. washThe combined CH2Cl2 layers are washed with NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oil which
  5. customis purified by column chromatography
  6. washeluting with EtOAc/hexane (4:6)

Sources & evidence

ORD record
ord-a5066636cf8b4786837a606f0f53ed81
Source dataset
uspto-grants-2003_05
Patent number
US06566381B1

Reaction notes

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