2-((Acetyloxy)methoxy)ethyl acetate → 9-(2-acetoxyethoxy)methyl-7-benzyl-N2-acetylguaninium acetate

HRID 355535

Reaction equation

N#N.[C:3]([NH:6][C:7]1[NH:8][C:9](=[O:23])[C:10]2[N:11]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:12]=[N:13][C:14]=2[N:15]=1)(=[O:5])[CH3:4].[C:24]([O:27][CH2:28][O:29][CH2:30][CH2:31][O:32][C:33](=[O:35])[CH3:34])(=[O:26])[CH3:25]>CN(C=O)C>[C:24]([O-:27])(=[O:26])[CH3:25].[C:33]([O:32][CH2:31][CH2:30][O:29][CH2:28][N:13]1[CH2:12][N:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]2[C:9](=[O:23])[NH2+:8][C:7]([NH:6][C:3](=[O:5])[CH3:4])=[N:15][C:14]1=2)(=[O:35])[CH3:34]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixed solution containing 100 mg (0.35 mmol) of N2 -acetyl-7-benzylguanine and 1 ml of DMF was added 64 mg (0.37 mmol) of (2-acetoxyethoxy)methyl acetate [prepared by the method described in M. J. Robins et al., Can. J. Chem., 60, 547 (1982)]. The mixture was heated at 80° C. for 20 h, and then allowed to cool. The reaction solution was concentrated, and purified by silica-gel column chromatography to yield 9-(2-acetoxyethoxy)methyl-7-benzyl-N2 -acetylguaninium acetate.

Workup

customprepared by the method
temperatureto cool
concentrationThe reaction solution was concentrated
custompurified by silica-gel column chromatography

Sources & evidence

ORD record: ord-d6cf45bdeaf249c694fd5fa4ce3a5c97
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05831092

Linked notes

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