2-Fluorothiophenol → HCID 10434433、化合物

HRID 547255

反応式

HRID 547255 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,5S,3R)-5-[(2-fluorophenylthio)methyl]oxolane-3,4-diol as a white powder.

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-4d3b175681e0492eac47b52da4c361c7
出典データセット
uspto-grants-2011_05
特許番号
US07939509B2

関連ノート

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