Water → HCID 86744924, compound

HRID 1087035Notes

Reaction equation

HRID 1087035 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4]([NH:18][CH2:19][CH:20]2[CH2:22][CH2:21]2)[N:3]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].O>CN(C)C=O>[C:23]([O:17][CH2:16][C@H:14]1[CH2:15][C@@H:11]([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([NH2:1])=[N:3][C:4]=3[NH:18][CH2:19][CH:20]2[CH2:22][CH2:21]2)[CH:12]=[CH:13]1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 57174705HCID 57174705, compound

Product 1

HCID 86744924HCID 86744924, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (%)-cis-4-(2 amino-6-(cyclopropylmethylamino)-9H-purin-9-yl)-2-cyclopentene-1-methanol from Example 7 (0.30 g, 1 mmol), acetic anhydride (0.204 g, 2 mmol), N,N-dimethylaminopyridine (0.005 g, 0.04 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature under nitrogen overnight. H2O (1 mL was added and the solution allowed to stir an additional hour, then concentrated under high vacuum. The residual oil was partitioned between saturated sodium bicarbonate solution (5 mL) and chloroform (3×50 mL). The combined chloroform extracts were dried (MgSO4), solvent evaporated and residue chromatographed on silica gel. Title compound was eluted with 4% methanol-chloroform; foamed from ethanol under high vacuum (0.330 g, 93%).

Workup

  1. concentrationconcentrated under high vacuum
  2. customThe residual oil was partitioned between saturated sodium bicarbonate solution (5 mL) and chloroform (3×50 mL)
  3. dry with materialThe combined chloroform extracts were dried (MgSO4), solvent
  4. customevaporated
  5. customresidue chromatographed on silica gel
  6. washTitle compound was eluted with 4% methanol-chloroform

Sources & evidence

ORD record
ord-8c7a88f5e6d64e0d8ba854a2ddd114fa
Source dataset
uspto-grants-1991_07
Patent number
US05034394

Reaction notes

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