m-Chloroperbenzoic acid → Methyl 2-[(4'-methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-3-phenylmethoxy-4,5-epoxypentanoate

HRID 413406Notes

Reaction equation

HRID 413406 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]([CH:24]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[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.ClC1C=C(C=CC=1)C(OO)=[O:40]>C(Cl)Cl.C(=O)(O)[O-].[Na+].O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]([S:15]([NH:18][CH:19]([CH:24]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:25]3[O:40][CH2:26]3)[C:20]([O:22][CH3:23])=[O:21])(=[O:16])=[O:17])=[CH:13][CH:14]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 23508244HCID 23508244, compound

Product 1

HCID 23508272Methyl 2-[(4'-methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-3-phenylmethoxy-4,5-epoxypentanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent3×

Procedure

The methyl 2-[(4′-methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-3-phenylmethoxy-4-pentenoate 63d (1.23 g, 2.48 mmol) is dissolved in methylene chloride (9 mL) and sodium bicarbonate (252 mg), in water (4 mL), then the reaction is cooled to 0° C. 3-Chloroperoxybenzoic acid is added slowly and the reaction is stirred for two hours. The substrate is still present so additional 3-chloroperoxybenzoic acid is added (1 g) along with 175 mg sodium bicarbonate and the reaction is stirred overnight. The mixture is diluted with aqueous sodium bicarbonate solution and methylene chloride and the layers are separated. The aqueous layer is washed with ethyl acetate (3 times) and the organic layers are combined and dried under reduced pressure. The resulting material is redissolved in ethyl acetate and washed with dilute sodium bicarbonate solution and then with brine, dried over magnesium sulfate and concentrated in vacuo to a light brown oil (2 g). The crude material is adsorbed onto silica gel and purified over a silica column eluting with hexane:ethyl acetate (8:2) followed with hexane:ethyl acetate (1:1). Product fractions are combined and dried to give the desired product.

Workup

  1. stirringthe reaction is stirred overnight
  2. customthe layers are separated
  3. washThe aqueous layer is washed with ethyl acetate (3 times)
  4. customdried under reduced pressure
  5. dissolutionThe resulting material is redissolved in ethyl acetate
  6. washwashed with dilute sodium bicarbonate solution
  7. dry with materialwith brine, dried over magnesium sulfate
  8. concentrationconcentrated in vacuo to a light brown oil (2 g)
  9. custompurified over a silica column
  10. washeluting with hexane:ethyl acetate (8:2)
  11. customdried

Sources & evidence

ORD record
ord-49baab0d6c0e49cbbe8aead09e6a236b
Source dataset
uspto-grants-2003_05
Patent number
US06566381B1

Reaction notes

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