Diethyl Ether → HCID 11059916, compound

HRID 582526Notes

Reaction equation

HRID 582526 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[C:42]2[N:41]=[C:40]([Cl:43])[N:39]=[C:23]([NH:24][CH2:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:22]=2[N:21]=[CH:20]1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].CCOCC>CO.O>[Cl:43][C:40]1[N:39]=[C:23]([NH:24][CH2:25][CH:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:22]2[N:21]=[CH:20][N:19]([C:42]=2[N:41]=1)[C@@H:6]1[O:7][C@H:8]([CH2:14][OH:15])[C@@H:9]([OH:10])[C@H:5]1[OH:4]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 13910512HCID 13910512, compound

Product 1

HCID 11059916HCID 11059916, compoundYield 11.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-Chloro-N-(2,2-diphenylethyl)-adenosine 2',3',5'-triacetate (2.0 g,3.29 mmol) was dissolved in methanol (120 ml) and the solution was stirred at room temperature with 2M aqueous sodium carbonate solution (10 ml). After 2h the mixture was diluted with water (350 ml) and extracted with ethyl acetate (2×10 ml). The extract was washed with water (100 ml) and dried (MgSO4) then evaporated to leave a froth (1.42 g). A sample (0.42 g) was purified by column chromatography on flash silica eluting with ethyl acetate:cyclohexane (3:1). Evaporation of appropriate fractions gave an oil which was treated with ether (20 ml) to give a solid, which was collected by filtration, washed with ether and dried in vacuo to give the title compound (0.177 g) as a solid [α]D -39° (CHCl3 c=1%).

Workup

  1. extractionextracted with ethyl acetate (2×10 ml)
  2. washThe extract was washed with water (100 ml)
  3. dry with materialdried (MgSO4)
  4. customthen evaporated
  5. customto leave a froth (1.42 g)
  6. customA sample (0.42 g) was purified by column chromatography on flash silica eluting with ethyl acetate:cyclohexane (3:1)
  7. customEvaporation of appropriate fractions
  8. customgave an oil which
  9. customto give a solid, which
  10. filtrationwas collected by filtration
  11. washwashed with ether
  12. customdried in vacuo

Sources & evidence

ORD record
ord-d813ed05578f447dbf3df0c1e8e69033
Source dataset
uspto-grants-1999_07
Patent number
US05925624

Reaction notes

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