Acetic Acid → HCID 178520987, compound

HRID 1747597Notes

Reaction equation

HRID 1747597 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[CH2:14][CH2:13][C@H:12]([O:15][C:16]2[N:24]=[CH:23][N:22]=[C:21]3[C:17]=2[N:18]=[C:19]([C:31]2[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH:34]=[CH:33][CH:32]=2)[N:20]3C2CCCCO2)[CH2:11]1)(C(C)(C)C)(C)C.O.CC(O)=O>C1COCC1>[C:31]1([C:19]2[NH:20][C:21]3[C:17]([N:18]=2)=[C:16]([O:15][C@H:12]2[CH2:13][CH2:14][C@H:10]([CH2:9][OH:8])[CH2:11]2)[N:24]=[CH:23][N:22]=3)[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 667978956-{[(1S,3S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentyl]oxy}-8-(1-naphthyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Product 1

HCID 178520987HCID 178520987, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-{[(1S,3S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-cyclopentyl]oxy}-8-(1-naphthyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (156.9 mg, 0.0002808 mol) in THF (3.8 mL) was added water (3.8 mL) and AcOH (7.6 mL), and the reaction mixture was stirred for 7 hours. The reaction mixture was quenched by the slow addition of saturated NaHCO3, and the resulting mixture was extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (0 to 5% MeOH/CH2Cl2) to obtain 85.7 mg (85%) of the title compound as a white solid. LC/MS: Rt=1.51 min, ES+ 361 (FA standard).

Workup

  1. customThe reaction mixture was quenched by the slow addition of saturated NaHCO3
  2. extractionthe resulting mixture was extracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (0 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c9de1bc66e8c4045a838f33ec625ba6b
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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