Carbon Dioxide → 2,2'-Anhydro-1-beta-arabinofuranosylthymine

HRID 722761

반응식

HRID 722761 반응식
[CH3:1][C:2]1[C:3](=[O:18])[NH:4][C:5](=[O:17])[N:6]([CH:16]=1)[C@@H:7]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1O.C(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.C(=O)=O.C(OCC)C>CN(C)P(N(C)C)(N(C)C)=O.C([O-])(O)=O.[Na+]>[CH3:1][C:2]1[C:3](=[O:18])[N:4]=[C:5]2[N:6]([C@@H:7]3[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@@H:8]3[O:17]2)[CH:16]=1

참가 물질

7

반응물 4

HCID 280Carbon DioxideHCID 3283Diethyl EtherHCID 7597Diphenyl carbonateHCID 4454085-Methyluridine

생성물 1

HCID 1680452,2'-Anhydro-1-beta-arabinofuranosylthymine수율 77.3%

시약·촉매·용매 2

HCID 516892Sodium Bicarbonate촉매HCID 12679Hexamethylphosphoramide용매

반응 조건

온도
150 °C

실험 절차

A mixture of 5-methyluridine (16.77 g, 69.2 mmol), diphenyl carbonate (17.8 g, 83.1 mmol) and NaHCO3 (100 mg) in hexamethylphosphoramide (175 mL) was heated to 150° C. with stirring until evolution of CO2 ceased (approximately 1 hour). The reaction mixture was cooled and then poured into diethyl ether (1 L) while stirring to furnish a brown gum. Repeated washings with diethyl ether (4×250 mL) furnished a straw-colored hygroscopic powder. The solid was purified by short column chromatography on silica gel (400 g). Pooling and concentrating appropriate fraction, which were eluted with CH2Cl2—MeOH (85:15), furnished the title compound as a straw-colored solid (12 g, 77.3%), which crystallized from EtOH as long needles, m.p. 226–227° C.

후처리

  1. custom(approximately 1 hour)
  2. temperatureThe reaction mixture was cooled
  3. customto furnish a brown gum
  4. washRepeated washings with diethyl ether (4×250 mL)
  5. customfurnished a straw-colored hygroscopic powder
  6. customThe solid was purified by short column chromatography on silica gel (400 g)
  7. concentrationPooling and concentrating appropriate fraction, which
  8. washwere eluted with CH2Cl2—MeOH (85:15)

출처 및 근거

ORD 기록
ord-f08c332356fe4bd3bbc9572ab3ee7d7d
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138517B2

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