Chloroacetonitrile → Descarboxymethyl Cyanomethyl Treprostinil

HRID 245601

反応式

HRID 245601 の反応式
[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

参加物

5

反応物 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 11174966Descarboxymethyl treprostinil

生成物 1

HCID 11314741Descarboxymethyl Cyanomethyl Treprostinil収率 82%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
30 °C

実験手順

(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%

後処理

  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

出典と根拠

ORDレコード
ord-bb79e61ee673448a99e72fa55b42804e
出典データセット
uspto-grants-2014_02
特許番号
US08658837B2

関連ノート

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