7387-57-7 → HCID 131713628, compound

HRID 358012Notes

Reaction equation

[CH3:1][O:2][C:3]1([O:11][CH3:12])[CH2:7][CH:6](OC)[NH:5][C:4]1=[O:10].[C:13]([O:16][C@@H:17]1[C@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@@H:20]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[O:19][C@H:18]1[N:31]1[C:40]2[N:39]=[CH:38][N:37]=[C:35]([NH2:36])[C:34]=2[N:33]=[CH:32]1)(=[O:15])[CH3:14]>C1C=CC=CC=1.CC(C)=O>[C:13]([O:16][C@@H:17]1[C@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@@H:20]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[O:19][C@H:18]1[N:31]1[C:40]2[N:39]=[CH:38][N:37]=[C:35]([NH:36][CH:6]3[NH:5][C:4](=[O:10])[C:3]([O:2][CH3:1])([O:11][CH3:12])[CH2:7]3)[C:34]=2[N:33]=[CH:32]1)(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 160 °C

Procedure

3,3,5-Trimethoxy-2-pyrrolidinone (445 mg) was evenly admixed with adenosine 2',3',5'-triacetate (1 g) and the mixture was melted and reacted by heating at 160° C. for 2 hours. The reaction mixture was then allowed to cool and subjected to silica gel column chromatography using benzene-acetone (2:1) as the eluent to give N6 -(3,3-dimethoxy-2-oxo-5-pyrrolidinyl)adenosine 2',3',5'-triacetate (1 g). This product was dissolved in ammonia-saturated methanol (30 ml) and left standing at 5° C. for 17 hours, after which time it was concentrated under reduced pressure. The residue was washed with benzene and the insolubles were subjected to silica gel column chromatography using chloroform-methanol (10:1) as the eluent. The active fractions were pooled and concentrated under reduced pressure to give crystals. Recrystallization from methanol-acetone yielded N6 -(3,3-dimethoxy-2-oxo-5-pyrrolidinyl)adenosine as colorless crystals (680 mg).

Workup

customreacted
temperatureto cool

Sources & evidence

ORD record: ord-0a00746d7ea1480db8254f183b076e37
Source dataset: uspto-grants-1984_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04464361

Reaction notes

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