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

HRID 17591

反応式

HRID 17591 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-301a33bb9e954fe5b3db7f6db18e61e7
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

関連ノート

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