Diethyl Ether → 2,2'-Anhydrouridine

HRID 634883ノート

反応式

HRID 634883 の反応式
[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)(O)[O-].[Na+].C(OCC)C>CN(C)P(N(C)C)(N(C)C)=O>[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

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 6029UridineHCID 516892Sodium Bicarbonate

生成物 1

HCID 8061382,2'-Anhydrouridine収率 92%

試薬・触媒・溶媒 1

HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
135 °C

実験手順

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 carbones (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 (3×1l). 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).

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was filtered off
  3. washThe solid was washed three times with ether (3×1l)
  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

出典と根拠

ORDレコード
ord-b23c33edb58a4d08a8541da4f9c81c73
出典データセット
uspto-grants-2001_02
特許番号
US06184364B2

反応ノート

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