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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1697007Generated: October 30, 2026

Phenylacetyl chloride → N-{(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-phenyl-acetamide

https://huagongshe.com/reaction/1697007

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPhenylacetyl chlorideHCID 7679—
ReactantDiisopropylethylamineHCID 81531—
Reactant(1S,2R,3S,5R)-3-Amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol hydrochlorideHCID 86622640—
ReactantHCID 178478404HCID 178478404—
SolventTetrahydrofuranHCID 8028—
ProductN-{(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-phenyl-acetamideHCID 86622644—

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 phenylacetyl chloride (0.026 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 (114 mg). LCMS (electrospray): m/z [MH+] 583.27

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08163754B2
Source datasetuspto-grants-2012_04
ORD IDord-0a9f57fbe20d492da5de9ac154dc27a6
Source noteuspto-grants-2012_04