Chloroacetonitrile → Descarboxymethyl Cyanomethyl Treprostinil

HRID 245601

반응식

HRID 245601 반응식
[OH:1][C@@H:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][CH2:4][C@@H:5]1[C@H:9]2[CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([OH:18])[C:16]=3[CH2:17][C@H:8]2[CH2:7][C@H:6]1[OH:19].C([O-])([O-])=O.[K+].[K+].Cl[CH2:32][C:33]#[N:34]>CC(C)=O>[OH:19][C@H:6]1[C@H:5]([CH2:4][CH2:3][C@@H:2]([OH:1])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C@H:9]2[CH2:10][C:11]3[C:16]([CH2:17][C@H:8]2[CH2:7]1)=[C:15]([O:18][CH2:32][C:33]#[N:34])[CH:14]=[CH:13][CH:12]=3

참가 물질

5

반응물 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 11174966Descarboxymethyl treprostinil

생성물 1

HCID 11314741Descarboxymethyl Cyanomethyl Treprostinil수율 82%

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
30 °C

실험 절차

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol (2 g, 0.005 mol) in dry acetone (20 ml) was treated with K2CO3 (2.07 g, 0.015 mol), chloroacetonitrile (0.64 ml, 0.010 mol) and tetrabutylbromide (0.32 g, 0.001 mmol). The mixture was heated at 30° C. overnight. Then, the reaction mixture was filtered with celite pad. The filtrate was evaporated off under vacuum. The crude product was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate as a gradient eluent. Yield: 82%

후처리

  1. filtrationThen, the reaction mixture was filtered with celite pad
  2. customThe filtrate was evaporated off under vacuum
  3. customThe crude product was purified by chromatography on silica gel using
  4. additiona mixture of hexane and ethyl acetate as a gradient eluent

출처 및 근거

ORD 기록
ord-bb79e61ee673448a99e72fa55b42804e
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658837B2

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