Acetoxyacetyl chloride → Acetic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentylcarbamoyl}-methyl ester

HRID 215861Notes

Reaction equation

HRID 215861 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][C@@H:6]([N:8]2[CH:16]=[N:15][C:14]3[C:9]2=[N:10][C:11]([Cl:32])=[N:12][C:13]=3[NH:17][CH2:18][CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:5]([OH:33])[C@@H:4]1[OH:34].[C:35]([O:38][CH2:39][C:40](Cl)=[O:41])(=[O:37])[CH3:36]>C1COCC1>[Cl:32][C:11]1[N:10]=[C:9]2[C:14]([N:15]=[CH:16][N:8]2[C@@H:6]2[CH2:7][C@H:3]([NH:2][C:40]([CH2:39][O:38][C:35](=[O:37])[CH3:36])=[O:41])[C@@H:4]([OH:34])[C@H:5]2[OH:33])=[C:13]([NH:17][CH2:18][CH:19]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:12]=1

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 86622640(1S,2R,3S,5R)-3-Amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol hydrochloride

Product 1

HCID 86637573Acetic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentylcarbamoyl}-methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(1S,2R,3S,5R)-3-Amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol hydrochloride (Intermediate GA3) (3.0 g, 5.6 mmol) is dissolved in dry THF (100 mL) and TEA (2.8 g, 28 mmol). Acetoxyacetylchloride (0.76 g, 5.6 mmol) is dissolved in dry THF (4 mL) and is added to the reaction mixture dropwise.

Workup

  1. additionis added to the reaction mixture dropwise

Sources & evidence

ORD record
ord-f467c82ab54749bd934e667293e295e0
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

Loading…