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Sodium Thiosulfate → (2R)-2-Allyloxycarbonylamino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]-1-butyl diallyl phosphate

HRID 1269393
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HRID 1269393 반응식
[CH2:1]([O:4][C:5]([NH:7][C@:8]([CH3:29])([CH2:11][CH2:12][C:13]1[O:14][C:15]([C:18]#[C:19][CH2:20][CH2:21][O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:16][CH:17]=1)[CH2:9][OH:10])=[O:6])[CH:2]=[CH2:3].N1C=NN=N1.C(N(C(C)C)[P:39]([O:44][CH2:45][CH:46]=[CH2:47])[O:40][CH2:41][CH:42]=[CH2:43])(C)C.ClC1C=CC=C(C(OO)=[O:59])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[P:39]([O:40][CH2:41][CH:42]=[CH2:43])([O:44][CH2:45][CH:46]=[CH2:47])([O:10][CH2:9][C@@:8]([NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])([CH3:29])[CH2:11][CH2:12][C:13]1[O:14][C:15]([C:18]#[C:19][CH2:20][CH2:21][O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:16][CH:17]=1)=[O:59]
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참가 물질

7

반응물 5

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 4686855Diallyl diisopropylphosphoramiditeHCID 66673269(2R)-2-Allyloxycarbonylamino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl) furan-2-yl]butan-1-olHCID 178418441HCID 178418441, 화합물

생성물 1

HCID 66672845
(2R)-2-Allyloxycarbonylamino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]-1-butyl diallyl phosphate
수율 81.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (2R)-2-allyloxycarbonylamino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]butan-1-ol (0.6202 g, 1.54 mmol) obtained in Example (26a) in dichloromethane (15 ml) were added successively 1H-tetrazole (0.7220 g, 10.31 mmol) and diallyl diisopropylphosphoramidite (0.81 ml, 3.06 mmol) with stirring under ice-cooling, and then the reaction mixture was stirred at room temperature for 2 hours. After stirring, to the reaction mixture was added m-chloroperbenzoic acid (content: 70%) (0.7556 g, 3.07 mmol) with stirring under ice cooling, and the resulting mixture was stirred at the same temperature for 10 minutes. After stirring, to the reaction mixture was added 10% aqueous sodium thiosulfate solution to quench the reaction, and the resulting mixture was extracted with dichloromethane. The extract was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (3:2) as the eluent to afford the title compound (0.7049 g, yield: 81%)

후처리

  1. temperaturecooling
  2. stirringthe reaction mixture was stirred at room temperature for 2 hours
  3. stirringAfter stirring, to the reaction mixture
  4. stirringwith stirring under ice cooling
  5. stirringthe resulting mixture was stirred at the same temperature for 10 minutes
  6. stirringAfter stirring, to the reaction mixture
  7. customto quench
  8. customthe reaction
  9. extractionthe resulting mixture was extracted with dichloromethane
  10. washThe extract was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationAfter filtration
  13. customthe solvent was removed in vacuo
  14. customthe residue was purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-ff0b7927ccdb4a3d902894e6010350be
출처 데이터셋
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07199150B2

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