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

HRID 1503308노트

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HRID 1503308 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 30088972',3'-Didehydro-3'-deoxy-4'-ethynylthymidine수율 91%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
37 °C

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-ec8d2e68a26c4540b5fd3ae691e980bf
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212174B2

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