HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzenepropanoyl chloride → N-{(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-3-phenyl-propionamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzenepropanoyl chloride | HCID 64801 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (1S,2R,3S,5R)-3-Amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol hydrochloride | HCID 86622640 | — |
| Reactant | HCID 178478404 | HCID 178478404 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-{(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-3-phenyl-propionamide | HCID 86622646 | — |
Reaction Steps
A solution of (1S,2R,3S,5R)-3-amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol hydrochloride (an intermediate for preparing the compound of Example 22) (100 mg, 0.2 mmol) in dry THF (1 ml) is treated with diisopropylethylamine (0.17 ml, 1 mmol) and 3-phenyl-propionyl chloride (0.03 ml, 0.2 mmol) and the mixture is stirred at room temperature for 18 hours. The solvent is removed under reduced pressure and the residue is dissolved in dichloromethane (2 ml) and washed with dilute hydrochloric acid (2 ml). The organic layer is separated and evaporated under reduced pressure to afford the title compound. LCMS (electrospray): m/z [MH+] 597.32
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08163754B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-cfd9f7fedb6b48029fe4e7b9990134ee |
| Source note | uspto-grants-2012_04 |