Potassium Carbonate → 2',3'-Didehydro-3'-deoxy-4'-ethynylthymidine

HRID 1503308ノート

反応式

HRID 1503308 の反応式
C(OC([O:8][CH2:9][C@@:10]1([C:24]#[CH:25])[O:14][C@@H:13]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH:12]=[CH:11]1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>CO>[C:24]([C@:10]1([CH2:9][OH:8])[O:14][C@@H:13]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH:12]=[CH:11]1)#[CH:25]

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 53372555(2R,5R)-5-t-butoxycarbonyloxymethyl-5-ethynyl-2-(thymin-1-yl)-2,5-dihydrofuran

生成物 1

HCID 30088972',3'-Didehydro-3'-deoxy-4'-ethynylthymidine収率 91%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
37 °C

実験手順

(2R,5R)-5-t-Butoxycarbonyloxymethyl-5-ethynyl-2-(thymin-1-yl)-2,5-dihydrofuran (5 g) was added to a glass reactor under nitrogen, and methanol (150 g) and potassium carbonate (9.9 g) were added. The mixture was stirred at 37° C. for 4 hours. The reaction mixture was concentrated and dissolved in water. Aqueous sodium hydroxide and toluene were added to the solution under stirring for phase separation, and hydrochloric acid and methyl ethyl ketone were added to the aqueous layer, followed by stirring for further phase separation. The thus-separated organic layer was concentrated, and the residue was purified through recrystallization from ethanol and heptane, to thereby yield 3.2 g of 4′-ethynyl-2′,3′-didehydro-3′-deoxythymidine (yield: 91%, β/α=>99/1). The 1H-NMR data of the compound are the same as those of the compound produced in Example 3.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in water
  3. additionAqueous sodium hydroxide and toluene were added to the solution
  4. stirringunder stirring for phase separation, and hydrochloric acid and methyl ethyl ketone
  5. additionwere added to the aqueous layer
  6. stirringby stirring for further phase separation
  7. concentrationThe thus-separated organic layer was concentrated
  8. customthe residue was purified through recrystallization from ethanol and heptane

出典と根拠

ORDレコード
ord-ec8d2e68a26c4540b5fd3ae691e980bf
出典データセット
uspto-grants-2015_12
特許番号
US09212174B2

反応ノート

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