Methanol → HCID 86589976, compound

HRID 1793252Notes

Reaction equation

HRID 1793252 reaction equation
C([Si](C)(C)[O:6][C@@H:7]1[C@@:11]([CH:31]([NH:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([CH2:12][O:13][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[O:10][C@@H:9]([N:48]2[CH:56]=[C:54]([CH3:55])[C:52](=[O:53])[NH:51][C:49]2=[O:50])[CH2:8]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>O1CCCC1>[C:34]1([CH2:33][NH:32][CH:31]([C@:11]2([CH2:12][OH:13])[O:10][C@@H:9]([N:48]3[CH:56]=[C:54]([CH3:55])[C:52](=[O:53])[NH:51][C:49]3=[O:50])[CH2:8][C@@H:7]2[OH:6])[NH:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2724141Tetrabutylammonium FluorideHCID 86589977HCID 86589977, compound

Product 1

HCID 86589976HCID 86589976, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3′-O-[(tertbutyl)dimethylsilyl]-5′-O-[(tertbutyl)diphenylsilyl]-4′-C-(1,1′-diphenylmethylaminomethyl)thymidine (2) (1.2 g, 1.5 mmol) was dissolved in tetrahydrofuran (50 mL) at ambient temperature. A solution of tetrabutylammonium fluoride in tetrahydrofuran (4.5 mL) was then added to the solution. The resulting mixture was stirred for 3 hours at ambient temperature. Methanol (5 mL) was then added and the reaction mixture concentrated under vacuum. The residue was purified by flash column chromatography (95:5 dichloromethane:methanol) to give the title compound (3) as an amorphous white solid (0.65 g, 100%) on removal of solvent from the appropriate fractions. δH(300 MHz, d6-DMSO) 11.23(1H, s, br, N3—H), 7.75(1H, s, H-6), 7.41–7.15(10H, m, Ph2CHNH), 6.21(1H, dd, H-1′), 5.57(1H, d, br, 3′-OH), 5.21(1H, t, 5′-OH), 4.78(1H, s, Ph2CHNH), 4.35(1H, m, H-3′), 3.61(2H, 2d, H-5′), 2.54(2H, 2d, 4′-C—CH2), 2.18(2H, m, H-2′), 1.75(3H, s, 5-CH3); δC(75.45 MHz, d6-DMSO) 150.46, 144.53, 144.28, 136.28, 128.36, 126.99, 126.74, 109.17, 88.39, 83.18, 66.79, 64.10, 54.91, 12.27.

Workup

  1. concentrationthe reaction mixture concentrated under vacuum
  2. customThe residue was purified by flash column chromatography (95:5 dichloromethane:methanol)

Sources & evidence

ORD record
ord-1bf0f83c98cd47049c28a4312f33317e
Source dataset
uspto-grants-2006_07
Patent number
US07078499B2

Reaction notes

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