Water → HCID 23508248, compound

HRID 413364Notes

Reaction equation

HRID 413364 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH:18]([CH2:23][CH:24]=[CH2:25])[C:19]([O:21][CH3:22])=[O:20])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.O.ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([NH:17][CH:18]([CH2:23][CH:24]3[O:35][CH2:25]3)[C:19]([O:21][CH3:22])=[O:20])(=[O:16])=[O:15])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 23508296HCID 23508296, compound

Product 1

HCID 23508248HCID 23508248, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent2×

Procedure

To a solution of methyl 2-[(4′-bromo[1,1′-biphenyl]-4-yl)-sulfonylamino]-pent-4-eneoate 13c (10.2 g, 24.1mmol) in CH2Cl2 (150 mL), NaHCO3 (11.0 g, 50 mmol) and water (140 mL) at 0° C., is slowly added m-chloroperbenzoic acid (57-86%) (19.4 g, ˜80 mmol). The reaction is stirred for 72 hours. The mixture is diluted with aqueous NaHCO3 and this mixture is extracted with ethyl acetate (3×250 mL). The combined ethyl acetate layer is washed with brine, dried over MgSO4, filtered and concentrated to an oil. Purification of this compound is accomplished by column chromatography with 40% ethyl acetate in hexanes as the eluent to give the desired product.

Workup

  1. customat 0° C.
  2. extractionthis mixture is extracted with ethyl acetate (3×250 mL)
  3. washThe combined ethyl acetate layer is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customPurification of this compound

Sources & evidence

ORD record
ord-f8308934a2154c5ab8b13376b2b28278
Source dataset
uspto-grants-2003_05
Patent number
US06566381B1

Reaction notes

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