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Bi(OTf)3 → (S)-1-chloro-3-(4-(2-(4-((R)-2,3-dihydroxypropoxy)phenyl)propan-2-yl)phenoxy)propan-2-yl acetate

HRID 705322
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HRID 705322 반응식
[C:1]([O:4][C@@H:5]([CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C@H:27]3[CH2:31][O:30]C(C)(C)[O:28]3)=[CH:21][CH:20]=2)([CH3:18])[CH3:17])=[CH:12][CH:11]=1)[CH2:6][Cl:7])(=[O:3])[CH3:2].[O-]S(C(F)(F)F)(=O)=O.[Bi+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C(#N)C>[C:1]([O:4][C@@H:5]([CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C@H:27]([OH:28])[CH2:31][OH:30])=[CH:21][CH:20]=2)([CH3:18])[CH3:17])=[CH:12][CH:11]=1)[CH2:6][Cl:7])(=[O:3])[CH3:2]
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참가 물질

4

반응물 2

HCID 9917655Bi(OTf)3HCID 117689799(S)-1-chloro-3-(4-(2-(4-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)propan-2-yl)phenoxy)propan-2-yl acetate

생성물 1

HCID 86293252(S)-1-chloro-3-(4-(2-(4-((R)-2,3-dihydroxypropoxy)phenyl)propan-2-yl)phenoxy)propan-2-yl acetate수율 86%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of crude (S)-1-chloro-3-(4-(2-(4-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)propan-2-yl)phenoxy)propan-2-yl acetate in anhydrous acetonitrile (8.0 mL) was added bismuth triflate (300 mg, 0.46 mmol) in one portion. After 0.5 h, the reaction mixture was partitioned twice with sodium bicarbonate and ethyl acetate. The organic phased were combined, dried over anhydrous magnesium sulfate, and filtered. Solvents were evaporated, and the resulting crude material was purified by silica gel flash chromatography (eluent: 2% to 5% methanol in dichloromethane) to provide the title compound (734 mg, 86%) as a sticky solid.

후처리

  1. customthe reaction mixture was partitioned twice with sodium bicarbonate and ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customSolvents were evaporated
  5. customthe resulting crude material was purified by silica gel flash chromatography (eluent: 2% to 5% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-7ec2554b501743619a49137ca3109f58
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09173939B2

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