HCID 90411273, compound → HCID 90412838, compound

HRID 1754624Notes

Reaction equation

HRID 1754624 reaction equation
[C:1]([N:9]1[C:14](=[O:15])[C:13]([CH3:16])=[CH:12][N:11]([C@H:17]2[CH2:21][CH2:20][C@H:19]([O:22][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[C@H:18]2[CH2:40][O:41]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:10]1=[O:61])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O.O>[C:1]([N:9]1[C:14](=[O:15])[C:13]([CH3:16])=[CH:12][N:11]([C@H:17]2[CH2:21][CH2:20][C@H:19]([OH:22])[C@H:18]2[CH2:40][OH:41])[C:10]1=[O:61])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 90411273HCID 90411273, compound

Product 1

HCID 90412838HCID 90412838, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 56 (0.45 g, 0.55 mmol) was dissolved in mixture of TFA (15 ml) and water (5 ml). The solution was stirred under argon for 1 h, then concentrated, co-evaporated 2 times with water to remove residual TFA and chromatographed on silica eluting with a gradient (5-7%) of MeOH in dichloromethane to yield nucleoside 57 (0.140 g, 75% yield) as a white solid. 1H NMR (DMSO-d6): δ7.95-7.92 (m, 2H), 7.80-7.74 (m, 2H), 7.57 (t, J=7.7 Hz, 2H), 4.96-4.86 (m, 1H), 4.81 (d, J=5.1 Hz, 1H), 4.62 (t, J=4.0, 1H), 3.95-3.88 (m, 1H), 3.50-3.45 (m, 1H), 3.35-3.25 (m, 1H), 2.12-1.98 (m, 4H), 1.86 (s, 3H), 1.48-1.38 (m, 1H).

Workup

  1. concentrationconcentrated
  2. customto remove residual TFA
  3. customchromatographed on silica eluting with a gradient (5-7%) of MeOH in dichloromethane

Sources & evidence

ORD record
ord-b99b925807624a42bec4704c4e7f8c69
Source dataset
uspto-grants-2015_10
Patent number
US09169256B2

Reaction notes

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