Diethyl Ether → HCID 11059916, compound

HRID 1420299Notes

Reaction equation

HRID 1420299 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 2 h the mixture was diluted with water (350 ml) and extracted with ethyl acetate (2×100 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 (2×100 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-8981e1f78b0a44b79a881b5cb2522afb
Source dataset
uspto-grants-1999_03
Patent number
US05889178

Reaction notes

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