Methanol → HCID 69177935, compound

HRID 1392012Notes

Reaction equation

HRID 1392012 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH2:38])[C:5]2[N:6]=[CH:7][N:8]([C:36]=2[N:37]=1)[C@@H:9]1[O:35][C@H:26]([CH2:27][O:28][Si](C(C)C)(C)C)[C@@H:18]([O:19][Si](C(C)C)(C)C)[C@H:10]1[O:11][Si](C(C)C)(C)C.Cl[C:40]1[CH:45]=[CH:44][C:43]([CH2:46][CH2:47][OH:48])=[CH:42][CH:41]=1.[H-].[Na+].CO.C(Cl)[Cl:54]>>[Cl:54][C:44]1[CH:45]=[CH:40][CH:41]=[CH:42][C:43]=1[CH2:46][CH2:47][O:48][C:2]1[N:3]=[C:4]([NH2:38])[C:5]2[N:6]=[CH:7][N:8]([C:36]=2[N:37]=1)[C@@H:9]1[O:35][C@H:26]([CH2:27][OH:28])[C@@H:18]([OH:19])[C@H:10]1[OH:11]

Participants

6

Reactant 5

HCID 887Methanol2×HCID 6344Dichloromethane3×HCID 24758Sodium hydrideHCID 74647p-Chlorophenethylic alcoholHCID 58661654HCID 58661654, compound

Product 1

HCID 69177935HCID 69177935, compoundYield 20.8%

Conditions

Temperature
50 °C

Procedure

A mixture of 2-chloro-2′,3′,5′-tris-O-(isopropyldimethylsilyl)adenosine (Example 5, 5.0 g, 6.5 mmol) and 15 ml of 2-(4-chlorophenyl)ethyl alcohol was placed under a nitrogen atmosphere and heated to 50° C. Sodium hydride (1.30 g, 60% dispersion in mineral oil, 32.5 mmol) was added at a rate so as to control gas evolution. The reaction was then heated for 48 h at which time LC showed conversion to the fully deprotected coupling product. The reaction was allowed to cool to room temperature, carefully quenched with 40 mL of water and extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with brine (120 mL), dried over MgSO4, and concentrated under reduced pressure to afford a clear oil. Chromatography on silica gel eluting with CH2Cl2, 5% MeOH in CH2Cl2, and then 10% MeOH in CH2Cl2 provided 570 mg (20.8%) of the title compound as a white solid. m.p. 158–161° C.

Workup

  1. temperatureThe reaction was then heated for 48 h at which time LC
  2. temperatureto cool to room temperature
  3. customcarefully quenched with 40 mL of water
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. washThe combined organic extracts were washed with brine (120 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto afford a clear oil

Sources & evidence

ORD record
ord-f4f19e9d6a1c4702817e7263561a2f3b
Source dataset
uspto-grants-2008_03
Patent number
US07342003B2

Reaction notes

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