2-Fluorothiophenol → HCID 10434433、化合物

HRID 916546

反応式

HRID 916546 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[OH:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[NH:15][C:16]1[N:24]=[CH:23][N:22]=[C:21]2[C:17]=1[N:18]=[CH:19][N:20]2[CH:25]1[C@H:29]([OH:30])[C@H:28]([OH:31])[C@@H:27]([CH2:32]Cl)[O:26]1>[OH-].[Na+].CN(C)C=O>[OH:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[NH:15][C:16]1[N:24]=[CH:23][N:22]=[C:21]2[C:17]=1[N:18]=[CH:19][N:20]2[CH:25]1[C@H:29]([OH:30])[C@H:28]([OH:31])[C@@H:27]([CH2:32][S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[O:26]1

参加物

5

反応物 2

HCID 5202162-FluorothiophenolHCID 671894862-{6-[((1R,2R)-2-hydroxycyclopentyl)amino]-purin-9-yl}(4S,5S,3R)-5-(chloromethyl)oxolane-3,4-diol

生成物 1

HCID 10434433HCID 10434433、化合物収率 85.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

To a solution of 2-fluorothiophenol (38 mL, 406 mmol) in 2N sodium hydroxide (100 mL) was added 2-{6-[((1R,2R)-2-hydroxycyclopentyl)amino]purin-9-yl}(4S,5S,3R)-5-(chloromethyl)oxolane-3,4-diol (15.0 g, 40.6 mmol) in N,N-dimethylformamide (120 mL). The mixture was warmed to 100 C for 4 hours, following the progress of the reaction by TLC. The N,N-dimethylformamide was removed under reduced pressure, and the remaining mixture was diluted with water (200 mL), neutralized with acetic acid, extracted with ethyl acetate (3×125 mL), and the combined organic layers were dried over MgSO4. After removing the solvent under reduced pressure the residue was triturated with diethyl ether and filtered, to afford 16 grams of 2-{6-[((1R,2R)-2-hydroxycyclopentyl)amino]purin-9-yl}(4S,5 S,3R)-5-[(2-fluorophenylthio)methyl]oxolane-3,4-diol as a white powder (85% yield).

後処理

  1. temperatureThe mixture was warmed to 100 C for 4 hours
  2. customthe progress of the reaction by TLC
  3. customThe N,N-dimethylformamide was removed under reduced pressure
  4. additionthe remaining mixture was diluted with water (200 mL)
  5. extractionextracted with ethyl acetate (3×125 mL)
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. customAfter removing the solvent under reduced pressure the residue
  8. customwas triturated with diethyl ether
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-7708bfa48b7543cd8670163582b4e2f7
出典データセット
uspto-grants-2007_09
特許番号
US07271157B2

関連ノート

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