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

HRID 413406노트

반응식

HRID 413406 반응식
[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

참가 물질

6

반응물 2

HCID 70297m-Chloroperbenzoic acid2회HCID 23508244HCID 23508244, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 516892Sodium Bicarbonate용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-49baab0d6c0e49cbbe8aead09e6a236b
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566381B1

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