Diethyl Ether → 2,2'-Anhydrouridine
Reaction equation
[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]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 135 °C
Procedure
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).
Workup
- temperatureAfter cooling to room temperature
- filtrationthe precipitate was filtered off
- washThe solid was washed three times with ether (3×1l)
- additionWater (1 l) was added to the filtrate
- customthe aqueous layer was separated
- extractionextracted three times with methylene chloride (3×1 l)
- customThe aqueous phase was evaporated to dryness
- customThe combined solids were recrystallized from hot methanol
Sources & evidence
- ORD record
- ord-b23c33edb58a4d08a8541da4f9c81c73
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06184364B2
Reaction notes
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