Hydrofluoric Acid → HCID 86607303, compound

HRID 552701Notes

Reaction equation

HRID 552701 reaction equation
[C:1]([O:4][C@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][Si](C(C)C)(C(C)C)C(C)C)[O:7][C@H:6]1[N:26]1[CH:34]=[N:33][C:32]2[C:27]1=[N:28][CH:29]=[N:30][C:31]=2[NH:35][C@@H:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:38][CH2:37]1)(=[O:3])[CH3:2].F>N1C=CC=CC=1.O1CCCC1>[C:1]([O:4][C@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][OH:15])[O:7][C@H:6]1[N:26]1[CH:34]=[N:33][C:32]2[C:27]1=[N:28][CH:29]=[N:30][C:31]=2[NH:35][C@@H:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:38][CH2:37]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14917Hydrofluoric AcidHCID 86607302HCID 86607302, compound

Product 1

HCID 86607303HCID 86607303, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

(2R,3S,4R,5R)-2-{6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-9H-purin-9-yl}-5-{[(triisopropylsilyl)oxy]methyl}tetrahydrofuran-3,4-diyl diacetate (0.305 g, 0.49 mmol) was stirred in pyridine (2 mL) and tetrahydrofuran (2 mL). Hydrofluoric acid in pyridine (2.0 M) was added (15 drops) and the reaction was stirred at room temperature for thirty minutes. The reaction was quenched using saturated sodium bicarbonate then extracted using ethyl acetate (3×10 mL). The organic layer was dried (Na2SO4), filtered and concentrated. The brown residue was purified by column chromatography (30-50% ethyl acetate/hexanes followed by ethyl acetate) to give the title compound as a white solid (0.188 g, 82%).

Workup

  1. customThe reaction was quenched
  2. extractionthen extracted
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe brown residue was purified by column chromatography (30-50% ethyl acetate/hexanes followed by ethyl acetate)

Sources & evidence

ORD record
ord-a56da4878b7d4f8084028960dd569b8c
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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