Benzoyl chloride → Benzoic acid 5-(6-benzoylamino-purin-9-yl)-4-fluoro-2-trityloxymethyl-tetrahydro-furan-3-yl ester
Reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[O:15][CH:14]([CH2:16][O:17][C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]([OH:37])[CH:12]1[F:38].[C:39](Cl)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:40]>N1C=CC=CC=1>[C:39]([NH:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[O:15][CH:14]([CH2:16][O:17][C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:13]([O:37][C:18](=[O:17])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]1[F:38])(=[O:40])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1Participants
4
Procedure
Compound 55.2 (18.2 mmol) in pyridine (180 mL) was treated with BzCl (6.33 mL, 54.6 mmol) and stirred overnight. The solvent was removed in vacuo and the solid was dissolved in EtOAc (100 mL) and washed with H2O (2×50 mL). The solution was dried over MgSO4, filtered, and subjected to Combiflash purification (SiO2, 330 g, 0-100% EtOAc-hexanes gradient) which afforded 55.3 as a white solid (13.0 g, 96%, two steps).