Sodium Thiosulfate → 2-Cyclopropyl-5-methyl-7-(3-oxocyclopentyl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17591

반응식

HRID 17591 반응식
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:26]#[N:27])[C:10]([CH3:25])=[C:11]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:12]=3[C@H:13]3[CH2:17][CH2:16][C@@H:15]([OH:18])[CH2:14]3)[N:8]=2)[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:26]#[N:27])[C:10]([CH3:25])=[C:11]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:12]=3[CH:13]3[CH2:17][CH2:16][C:15](=[O:18])[CH2:14]3)[N:8]=2)[CH2:2][CH2:3]1

참가 물질

6

반응물 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 685843982-Cyclopropyl-7-[(1S*,3R*)-3-hydroxycyclopentyl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

생성물 1

HCID 685859442-Cyclopropyl-5-methyl-7-(3-oxocyclopentyl)-6-phenyl-1,3-benzoxazole-4-carbonitrile수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-Cyclopropyl-7-[(1S*,3R*)-3-hydroxycyclopentyl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-302) (50 mg, 0.14 mmol) was dissolved in dichloromethane (1 ml), and at 0° C., Dess-Martin reagent (118 mg, 0.28 mmol) was added. The solution was stirred at room temperature for 3 hours, then again cooled at 0° C., and aqueous saturated sodium thiosulfate solution and an aqueous saturated sodium hydrogencarbonate solution were added, followed by further stirring for 10 minutes. The solution was extracted three times with dichloromethane. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=3:1, v/v) to obtain the entitled compound (44 mg, 89%) as a white solid.

후처리

  1. temperatureagain cooled at 0° C.
  2. stirringby further stirring for 10 minutes
  3. extractionThe solution was extracted three times with dichloromethane
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away
  8. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

출처 및 근거

ORD 기록
ord-301a33bb9e954fe5b3db7f6db18e61e7
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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