HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → N-(2-{9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}ethyl)methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | (2R,3R,4S,5R)-2-{2-(2-Aminoethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol | HCID 9957801 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-(2-{9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}ethyl)methanesulfonamide | HCID 9873080 | 67.9% |
Reaction Steps
Methanesulfonyl chloride (27 mg, 0.22 mmol) was added to a stirred solution of (2R,3R,4S,5R)-2-{2-(2-aminoethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (120 mg, 0.23 mmol) (Example 11) and triethylamine (0.1 ml, 0.72 mmol) in dichloromethane (10 ml). The reaction mixture was stirred at room temperature for 2 hr when the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol (98:2) increasing in polarity to (95:5). This gave the title compound (87 mg) as a powder. MS: 583 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06326359B1 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-b692a9335ff3411c8bcc5e51c419a3ab |
| Source note | uspto-grants-2001_12 |