Dicyclohexylcarbodiimide → (R)-2-benzyloxy-N-[(1S,2R,3S,4R)-4-(2,6-dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide

HRID 2382460Notes

Reaction equation

HRID 2382460 reaction equation
[CH2:1]([O:8][C@H:9]([CH3:13])[C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:29][C@H:30]1[CH2:34][C@@H:33]([N:35]2[CH:43]=[N:42][C:41]3[C:36]2=[N:37][C:38]([Cl:45])=[N:39][C:40]=3[Cl:44])[C@H:32]([OH:46])[C@@H:31]1[OH:47]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:1]([O:8][C@H:9]([CH3:13])[C:10]([NH:29][C@H:30]1[CH2:34][C@@H:33]([N:35]2[CH:43]=[N:42][C:41]3[C:36]2=[N:37][C:38]([Cl:45])=[N:39][C:40]=3[Cl:44])[C@H:32]([OH:46])[C@@H:31]1[OH:47])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 7000104(2R)-2-phenylmethoxypropanoic acidHCID 86622628(1S,2R,3S,5R)-3-amino-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol

Product 1

HCID 86647544(R)-2-benzyloxy-N-[(1S,2R,3S,4R)-4-(2,6-dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The title compound is prepared by dissolving (R)-2-benzyloxy-propionic acid (1 equivalent) in dichloromethane with 1,3-dicyclohexylcarbodiimide (1 equivalent) and a catalytic amount of 4-dimethylaminopyridine, stirring for five minutes, then adding (1S,2R,3S,5R)-3-amino-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol (Intermediate J5; 1-equivalent) in dichloromethane. The reaction is stirred at room temperature until determined to be complete, the solvent is removed under reduced pressure, and the title compound purified by column chromatography/crystallisation.

Workup

  1. customthe solvent is removed under reduced pressure
  2. customthe title compound purified by column chromatography/crystallisation

Sources & evidence

ORD record
ord-324d573c743a4d68bb4d007a90c00124
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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