Diethyl Ether → 2,2'-Anhydrouridine

HRID 618961노트

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HRID 618961 반응식
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1O.C(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.C(OCC)C>CN(C)P(N(C)C)(N(C)C)=O.C(=O)(O)[O-].[Na+]>[CH:16]1[C:14](=[O:15])[N:13]=[C:11]2[N:10]([C@@H:1]3[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@@H:2]3[O:12]2)[CH:17]=1

참가 물질

6

반응물 3

HCID 3283Diethyl EtherHCID 6029UridineHCID 7597Diphenyl carbonate

생성물 1

HCID 8061382,2'-Anhydrouridine수율 92%

시약·촉매·용매 2

HCID 516892Sodium Bicarbonate촉매HCID 12679Hexamethylphosphoramide용매

반응 조건

온도
135 °C

실험 절차

To a suspension of uridine (200 g, 819 mmoles) in hexamethylphosphoramide (HMPA) (400 ml) was added sodium bicarbonate (5.3 g, 63.1 mmoles, 0.077 equivalents (eq.)) and diphenyl carbonate (228.1 g, 1064.7 mmoles, 1.3 eq.). The mixture was heated to 135° C. for 11 h. After cooling to room temperature, diethyl ether (2 l) was added and the precipitate was filtered off. The solid was washed three times with ether (3×1 l). Water (1 l) was added to the filtrate, the aqueous layer was separated and extracted three times with methylene chloride (3×1 l). The aqueous phase was evaporated to dryness. The combined solids were recrystallized from hot methanol to yield 170 g (92%) of 2,2'-anhydrouridine. The spectral properties agreed with those reported in the literature (Hampton and Nichol (1966) Biochemistry 5:2076).

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was filtered off
  3. washThe solid was washed three times with ether (3×1 l)
  4. additionWater (1 l) was added to the filtrate
  5. customthe aqueous layer was separated
  6. extractionextracted three times with methylene chloride (3×1 l)
  7. customThe aqueous phase was evaporated to dryness
  8. customThe combined solids were recrystallized from hot methanol

출처 및 근거

ORD 기록
ord-8ed63517b616456e8fd8b87eea9152be
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05958691

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