Water → HCID 69828189, compound

HRID 1839255Notes

Reaction equation

HRID 1839255 reaction equation
CC1(C)[O:6][C@H:5]2[C@@H:7]([C:25]3[O:29][N:28]=[C:27]([CH3:30])[N:26]=3)[O:8][C@@H:9]([N:10]3[CH:18]=[N:17][C:16]4[C:11]3=[N:12][CH:13]=[N:14][C:15]=4[NH:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C@@H:4]2[O:3]1.FC(F)(F)C(O)=O.O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH:20]1([NH:19][C:15]2[N:14]=[CH:13][N:12]=[C:11]3[C:16]=2[N:17]=[CH:18][N:10]3[C@H:9]2[C@H:4]([OH:3])[C@H:5]([OH:6])[C@@H:7]([C:25]3[O:29][N:28]=[C:27]([CH3:30])[N:26]=3)[O:8]2)[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 69828738HCID 69828738, compound

Product 1

HCID 69828189HCID 69828189, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-{9-[(3aR,4R,6S,6aR)-2,2-dimethyl-6-(3-methyl-1,2,4-oxadiazol-5-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-N-cyclopentylamine (63 mg), trifluoroacetic acid (1 ml) and water (0.1 ml) was stirred at 0° for 6 h and then diluted with ethyl acetate (20 ml). The mixture was neutralised with sodium bicarbonate solution and the aqueous phase was extracted with ethyl acetate (2×10 ml). The combined organic extracts were washed with water (8 ml) and brine (10 ml) and dried (MgSO4). After concentration in vacuo the residue was purified by flahs column chromatography on silica gel, eluting with ethyl acetate:methanol (19:1) to give the title compound as a white foam (42 mg).

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (2×10 ml)
  2. washThe combined organic extracts were washed with water (8 ml) and brine (10 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationAfter concentration in vacuo the residue
  5. customwas purified by flahs column chromatography on silica gel
  6. washeluting with ethyl acetate:methanol (19:1)

Sources & evidence

ORD record
ord-a71f9f20cf0e4f09984fb0549918cfd1
Source dataset
uspto-grants-2004_01
Patent number
US06677316B2

Reaction notes

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