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m-Chloroperbenzoic acid → 3-[(S)-1-(4-Bromo-2-methyl-phenyl)-ethyl]-(S)-6-(2-methyl-oxiranylmethyl)-6-phenyl-[1,3]oxazinan-2-one

HRID 1640864
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HRID 1640864 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:22][C:23]([CH3:25])=[CH2:24])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12][C:11]2=[O:26])[CH3:9])=[C:4]([CH3:27])[CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:33]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:22][C:23]3([CH3:25])[CH2:24][O:33]3)([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[O:12][C:11]2=[O:26])[CH3:9])=[C:4]([CH3:27])[CH:3]=1
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참가 물질

4

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HCID 70297m-Chloroperbenzoic acidHCID 581023693-[(S)-1-(4-Bromo-2-methyl-phenyl)-ethyl]-(R)-6-(2-methyl-allyl)-6-phenyl-[1,3]oxazinan-2-one

생성물 1

HCID 581023913-[(S)-1-(4-Bromo-2-methyl-phenyl)-ethyl]-(S)-6-(2-methyl-oxiranylmethyl)-6-phenyl-[1,3]oxazinan-2-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
5 °C

실험 절차

3-[(S)-1-(4-Bromo-2-methyl-phenyl)-ethyl]-(R)-6-(2-methyl-allyl)-6-phenyl -[1,3]oxazin-an-2-one (1.34 g) dissolved in dichloromethane (15 mL) was added to a solution of 3-chloroperoxybenzoic acid (77%, 0.81 g) in dichloromethane (15 mL) cooled to 5° C. The cooling bath was removed and the solution was stirred at room temperature overnight. Aqueous 10% Na2S2O3 solution (10 mL) and aqueous saturated NaHCO3 solution (25 mL) were added and the resulting mixture was stirred for further 30 min. The organic phase was separated and washed with aqueous Na2S2O3 solution combined with aqueous saturated NaHCO3 solution, water, and brine. The organic phase was dried (MgSO4) and concentrated to furnish the title compound. Yield: 1.55 g (ca. 85-90% pure); LC-MS (Method 4): tR=4.28 min; Mass spectrum (ESI+): m/z=444/446 (Br) [M+H]+.

후처리

  1. customThe cooling bath was removed
  2. additionAqueous 10% Na2S2O3 solution (10 mL) and aqueous saturated NaHCO3 solution (25 mL) were added
  3. stirringthe resulting mixture was stirred for further 30 min
  4. customThe organic phase was separated
  5. washwashed with aqueous Na2S2O3 solution
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4c0db20f023f4a789983aa2efb981916
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08114868B2

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