Acetic Anhydride → HCID 136153480, compound

HRID 1087041Notes

Reaction equation

HRID 1087041 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][C@@H:6]([N:8]2[CH:16]=[N:15][C:14]3[C:13](=[O:17])[NH:12][C:11]([NH2:18])=[N:10][C:9]2=3)[CH:5]=[CH:4]1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:19]([O:1][CH2:2][C@H:3]1[CH2:7][C@@H:6]([N:8]2[CH:16]=[N:15][C:14]3[C:13](=[O:17])[NH:12][C:11]([NH2:18])=[N:10][C:9]2=3)[CH:5]=[CH:4]1)(=[O:21])[CH3:20]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 135433604(-)-Carbovir

Product 1

HCID 136153480HCID 136153480, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

(1R,4S)-9-(4-Hydroxymethyl-2-cyclopentenyl)guanine (150 mg, 0.607 mmole), acetic anhydride (freshly distilled, 65 mg, 0.161 mmole), 4-dimethylaminopyridine (3 mg), and dry dimethylformamide (5 mL) were stirred under nitrogen for 2 days. The solvent was evaporated and the residue applied to a silica gel column. Title compound was eluted with 10% methanol-chloroform as a waxy white solid. Crystallization from ethanol gave white powder (123 mg, 70%), m.p. 247°-249° C.; 1H-NMR (DMSO-d6) δ10.55 (br s, 1, NHCO), 7.55 (s, 1, purine H-8), 6.42 (br s, 2, NH2), 6.06 and 5.94 (both m, 2, CH=CH), 5.34 (m, 1, CH--N), 4.07 (d, J=6.0, 2, CH2O), 3.05 (m, 1, CH), 2.6 and 1.55 (both m, 2, CH2), 1.98 (s, 3, COCH3).

Workup

  1. customThe solvent was evaporated
  2. washTitle compound was eluted with 10% methanol-chloroform as a waxy white solid
  3. customCrystallization from ethanol

Sources & evidence

ORD record
ord-755df5d135e1443dbaf3af391e896b22
Source dataset
uspto-grants-1991_07
Patent number
US05034394

Reaction notes

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