Ammonia → HCID 89650994, compound
Reaction equation
C([O:9][C@H:10]1[C@:14]([F:16])([CH3:15])[C@H:13]([N:17]2[CH:22]=[CH:21][C:20](=[O:23])[NH:19][C:18]2=[O:24])[O:12][C@@:11]1([F:34])[CH2:25]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.N.C[OH:37]>>[F:16][C@:14]1([CH3:15])[C@H:10]([OH:9])[C@@:11]([F:34])([CH2:25][OH:37])[O:12][C@H:13]1[N:17]1[CH:22]=[CH:21][C:20](=[O:23])[NH:19][C:18]1=[O:24]Participants
4
Procedure
Chiral (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,4-difluor-O-2-benzoylmethyl-4-methyl-tetrahydrofuran-3-yl benzoate (0.34 g, 0.7 mmol) was dissolved into methanol, and a solution of ammonia in methanol (7 N, 20 mL) was added. The reaction mixture was stirred at room temperature for overnight. The mixture was concentrated, and the residue was purified by silica gel column chromatography (DCM:MeOH=20:1) and pre-HPLC to afford the title compound as a white solid (0.074 g, 38%).