Propionyl chloride → N-[(1S,2R,3S,4R)-4-(2,6-Dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide

HRID 1696986Notes

Reaction equation

HRID 1696986 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@H:9]1[CH2:13][C@@H:12]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([Cl:24])=[N:18][C:19]=3[Cl:23])[C@H:11]([OH:25])[C@@H:10]1[OH:26].[C:27](Cl)(=[O:30])[CH2:28][CH3:29].FC(F)(F)C(O)=O.NC1N=C(Cl)N=C2C=1N=CN2[C@@H]1C[C@H](NC(=O)CC)[C@@H](O)[C@H]1O>>[Cl:24][C:17]1[N:16]=[C:15]2[C:20]([N:21]=[CH:22][N:14]2[C@@H:12]2[CH2:13][C@H:9]([NH:8][C:27](=[O:30])[CH2:28][CH3:29])[C@@H:10]([OH:26])[C@H:11]2[OH:25])=[C:19]([Cl:23])[N:18]=1

Participants

4

Reactant 3

HCID 62324Propionyl chlorideHCID 86622625N-[(1S,2R,3S,4R)-4-(6-amino-2-chloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide trifluoroacetateHCID 86622627(1S,2R,3S,5R)-3-Amino-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol trifluoroacetate

Product 1

HCID 86622629N-[(1S,2R,3S,4R)-4-(2,6-Dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide

Procedure

The title compound is prepared from (1S,2R,3S,5R)-3-amino-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol trifluoroacetate and propionyl chloride using a procedure analogous to that used to prepare N-[(1S,2R,3S,4R)-4-(6-amino-2-chloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide trifluoroacetate in Example 2. MS (ES+) m/e 360 (MH+).

Sources & evidence

ORD record
ord-25d22acb63054d60908877cad0c3cbec
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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