Potassium Cyanide → 2-{9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}acetonitrile

HRID 2268420ノート

反応式

HRID 2268420 の反応式
[C-:1]#[N:2].[K+].CS(O[CH2:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[C@H:19]2[C@H:23]([OH:24])[C@H:22]([OH:25])[C@@H:21]([CH2:26][O:27][CH3:28])[O:20]2)=[C:12]([NH:29][CH2:30][CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:11]=1)(=O)=O>CN(C)C=O>[OH:24][C@@H:23]1[C@H:22]([OH:25])[C@@H:21]([CH2:26][O:27][CH3:28])[O:20][C@H:19]1[N:16]1[CH:15]=[N:14][C:13]2[C:17]1=[N:18][C:10]([CH2:9][C:1]#[N:2])=[N:11][C:12]=2[NH:29][CH2:30][CH:31]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

参加物

4

反応物 2

HCID 9032Potassium CyanideHCID 59975278{9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate

生成物 1

HCID 599752932-{9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}acetonitrile収率 63.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

Potassium cyanide (22 mg, 0.33 mmol) was added to a stirred solution of {9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate (130 mg, 0.22 mmol) (preparation 25) in N,N-dimethylformamide (3 ml). The reaction mixture was heated to 70° C. for 1.5 hr, allowed to cool to room temperature and then partitioned between diethyl ether and water. The aqueous layer was washed with diethyl ether. The combined organic solutions were washed with brine and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give a residue that was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (97:3). This gave the title compound (70 mg) as a powder. MS: 523 (MNa+).

後処理

  1. temperatureto cool to room temperature
  2. custompartitioned between diethyl ether and water
  3. washThe aqueous layer was washed with diethyl ether
  4. washThe combined organic solutions were washed with brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto give a residue that
  8. customwas purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (97:3)

出典と根拠

ORDレコード
ord-88136f73d9ad476d8c23f168e1eb71b0
出典データセット
uspto-grants-2001_12
特許番号
US06326359B1

反応ノート

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