Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Propanesulfonyl chloride, 2-methyl- | HCID 182236 | — |
| Reactant | (2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol | HCID 9897827 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 9830350 | HCID 9830350 | 59.9% |
Reaction Steps
(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (300 mg, 0.61 mmol) was dissolved in dry tetrahydrofuran (20 ml) (using gentle heating), a solution of 2-methyl-1-propanesulphonyl chloride (50 mg, 0.32 mmol) in dry tetrahydrofuran (2.5 ml) added and the mixture stirred at room temperature for 18 hr under a nitrogen atmosphere. A solution of triethylamine (100 mg, 0.98 mmol) and 2-methyl-1-propanesulphonyl chloride (50 mg, 0.32 mmol) in dry tetrahydrofuran (5 ml) was added and the resulting mixture stirred for a further 5 hr. The solvent was then removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (97:3), to give the product as a foam (117 mg). MS: 611 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06326359B1 |
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| Source dataset | uspto-grants-2001_12 |
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| ORD ID | ord-0f4d569a20d84a0f812874f6116e02ba |
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| Source note | uspto-grants-2001_12 |
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