2',3',5'-tri-O-acetyladenosine → N6-(2-oxo-3,3-dimethoxy-4-chloro-5-pyrrolidinyl)adenosine 2',3',5'-triacetate

HRID 358014Notes

Reaction equation

HRID 358014 reaction equation
[CH3:1][O:2][C:3]1([O:12][CH3:13])[CH:7]([Cl:8])[CH:6](OC)[NH:5][C:4]1=[O:11].[C:14]([O:17][C@@H:18]1[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@@H:21]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[O:20][C@H:19]1[N:32]1[C:41]2[N:40]=[CH:39][N:38]=[C:36]([NH2:37])[C:35]=2[N:34]=[CH:33]1)(=[O:16])[CH3:15]>CCCCCC.CC(C)=O>[C:14]([O:17][C@@H:18]1[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@@H:21]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[O:20][C@H:19]1[N:32]1[C:41]2[N:40]=[CH:39][N:38]=[C:36]([NH:37][CH:6]3[NH:5][C:4](=[O:11])[C:3]([O:2][CH3:1])([O:12][CH3:13])[CH:7]3[Cl:8])[C:35]=2[N:34]=[CH:33]1)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 965032',3',5'-tri-O-acetyladenosineHCID 129469943,3,5-Trimethoxy-4-chloro-2-pyrrolidinone

Product 1

HCID 131713629N6-(2-oxo-3,3-dimethoxy-4-chloro-5-pyrrolidinyl)adenosine 2',3',5'-triacetateYield 63.2%

Reagents, catalysts & solvents 1

HCID 21880519Acetone hexaneSolvent

Procedure

3,3,5-Trimethoxy-4-chloro-2-pyrrolidinone (500 mg) was evenly admixed with adenosine 2',3',5'-triacetate (940 mg) and the mixture was melted and reacted at 170° C. for 1 hour. The reaction mixture was subjected to silica gel column chromatography using hexane-acetone (1:1) as the eluent to obtain N6 -(2-oxo-3,3-dimethoxy-4-chloro-5-pyrrolidinyl)adenosine 2',3',5'-triacetate (860 mg). This product was dissolved in ammonia-saturated methanol (40 ml) and allowed to stand at 5° C. for 15 hours, at the end of which time the solvent was distilled off. The residue was washed with chloroform 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 N6 -(2-oxo-3,3-dimethoxy-4-chloro-5-pyrrolidinyl)adenosine (590 mg).

Workup

  1. customreacted at 170° C. for 1 hour

Sources & evidence

ORD record
ord-d2864b25f8c94b69a3f25b068f5b9efc
Source dataset
uspto-grants-1984_08
Patent number
US04464361

Reaction notes

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