Cyclopentylamine → (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-[6-(cyclopentylamino)-2-iodopurin-9-yl]oxolan-3-yl acetate

HRID 1724637Notes

Reaction equation

HRID 1724637 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([I:29])=[N:23][C:24]=2Cl)(=[O:3])[CH3:2].[CH:30]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31]1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[C:11]([O:10][C@H:9]1[C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[C@H:6]([N:19]2[CH:27]=[N:26][C:25]3[C:20]2=[N:21][C:22]([I:29])=[N:23][C:24]=3[NH:35][CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[O:7][C@@H:8]1[CH2:14][O:15][C:16](=[O:18])[CH3:17])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 81531DiisopropylethylamineHCID 482588Acetic acid (2R,3R,4R,5R)-3,4-diacetoxy-5-(6-chloro-2-iodo-purin-9-YL)-tetrahydro-furan-2-ylmethyl ester

Product 1

HCID 14886862(2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-[6-(cyclopentylamino)-2-iodopurin-9-yl]oxolan-3-yl acetateYield 71.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-(6-chloro-2-iodopurin-9-yl)oxolan-3-yl acetate (1.15 g, 2.13 mmol) in N,N-dimethylformamide (20 ml) was added cyclopentylamine (0.42 ml, 4.26 mmol) and diisopropylethylamine (10 ml), and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the residue chromatographed on a silica gel column, eluting with a mixture of 40% ethanol/60% hexane, to provide (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-[6-(cyclopentylamino)-2-iodopurin-9-yl]oxolan-3-yl acetate (0.9 g), a compound of formula (4).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue chromatographed on a silica gel column
  3. washeluting with a mixture of 40% ethanol/60% hexane

Sources & evidence

ORD record
ord-ecb417beea654c5a9e15ff8c2fd27ab7
Source dataset
uspto-grants-2009_02
Patent number
US07488720B2

Reaction notes

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