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

HRID 413357Notes

Reaction equation

HRID 413357 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]([CH2:24][CH:25]=[CH2:26])[C:20]([O:22][CH3:23])=[O:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.O.ClC1C=CC=C(C(OO)=[O:36])C=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]([CH2:24][CH:25]3[O:36][CH2:26]3)[C:20]([O:22][CH3:23])=[O:21])(=[O:16])=[O:17])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 23508232Methyl 2-[(4'-methoxy[1,1'-biphenyl]-4-yl)sulfonylamino]-pent-4-enoate

Product 1

HCID 12073922Methyl 2-[(4'-methoxy[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-[(4′-methoxy[1,1′-biphenyl]-4-yl)sulfonylamino]-pent-4-enoate 1(15.3 g, 40.8 mmol) in CH2Cl2(150 mL), NaHCO3 (7.1 g, 85 mmol) and water (80 mL) at 0° C., is added slowly m-chloroperbenzoic acid (32.6 g, ˜123 mmol, 57-86%). The reaction mixture is stirred overnight. The reaction is then diluted with aqueous NaHCO3 and the mixture is extracted three times with EtOAc. The combined EtOAc layer is washed with NaHCO3, brine, dried over MgSO4 and concentrated to an oil. Purification is accomplished by column chromatography with EtOAc/hexane (3:7 to 6:4) as the eluent to give the desired product as a mixture of two isomers (ratio 2:3).

Workup

  1. extractionthe mixture is extracted three times with EtOAc
  2. washThe combined EtOAc layer is washed with NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oil
  5. customPurification

Sources & evidence

ORD record
ord-b3f975b4c24d440db28788c83eab12aa
Source dataset
uspto-grants-2003_05
Patent number
US06566381B1

Reaction notes

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