Methanol → HCID 136351311, compound

HRID 1956818Notes

Reaction equation

HRID 1956818 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([CH2:15][O:16]C(=O)C)[O:8][C@@H:7]([N:20]2[CH:28]=[N:27][C:26]3[C:25](=[O:29])[NH:24][C:23]([NH:30]C(=O)C)=[N:22][C:21]2=3)[C@@H:6]1[NH:34]C(=O)C(F)(F)F)(=O)C.CCN(CC)CC.CO>O>[NH2:34][C@@H:6]1[C@@H:5]([OH:4])[C@H:10]([OH:11])[C@@H:9]([CH2:15][OH:16])[O:8][C@H:7]1[N:20]1[CH:28]=[N:27][C:26]2[C:25](=[O:29])[NH:24][C:23]([NH2:30])=[N:22][C:21]1=2

Participants

5

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 135431010HCID 135431010, compound

Product 1

HCID 136351311HCID 136351311, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 14.56 g (25.35 mmol) of N-[9-[3,4,6-tris-O-acetyl-2-deoxy-2-[(trifluoroacetyl)amino]-β-D-glucopyranosyl]-6,9-dihydro-6-oxo 1H-purin-2-yl]-acetamide was added a solution composed of 45 mL of Et3N, 225 mL of CH3OH, and 180 mL of H2O. This solution was stirred at room temperature for 12 hours. At this time, the solution was concentrated to dryness in vacuo. The residue was recrystallized from H2O yielding a white powder (7.2 g, 69%). To 7.08 g of this white powder was added 140 mL of 30% (wt/vol) NH4OH, and the reaction mixture was stirred for 15 hours at room temperature. The reaction mixture was then concentrated to dryness in vacuo. To the residue was added H2O and the mixture was frozen and lyophilized to a white powder yielding 9-(2-amino-2-deoxy-β-D-glucopyranosyl)guanine quantitatively. FAB-MS: m/z 313 for (M+1)+.

Workup

  1. concentrationAt this time, the solution was concentrated to dryness in vacuo
  2. customThe residue was recrystallized from H2O yielding a white powder (7.2 g, 69%)
  3. additionTo 7.08 g of this white powder was added 140 mL of 30% (wt/vol) NH4OH
  4. stirringthe reaction mixture was stirred for 15 hours at room temperature
  5. concentrationThe reaction mixture was then concentrated to dryness in vacuo
  6. additionTo the residue was added H2O
  7. temperaturethe mixture was frozen

Sources & evidence

ORD record
ord-15b9b7ec75e34088aabdf2ef9fd3cd4b
Source dataset
uspto-grants-1998_07
Patent number
US05780607

Reaction notes

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