Acetic Anhydride → (2R,3S,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl acetate

HRID 2205185Notes

Reaction equation

[CH3:1][C:2](OC(C)=O)=[O:3].[CH2:8]([O:15][C@@H:16]1[C@:20]([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([CH:21]([F:23])[F:22])[O:19][C@@H:18]([N:33]2[CH:38]=[CH:37][C:36](=[O:39])[NH:35][C:34]2=[O:40])[C@H:17]1[OH:41])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:2]([O:41][C@H:17]1[C@H:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@:20]([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([CH:21]([F:22])[F:23])[O:19][C@H:18]1[N:33]1[CH:38]=[CH:37][C:36](=[O:39])[NH:35][C:34]1=[O:40])(=[O:3])[CH3:1]

Participants

Conditions

Temperature: 20 °C

Procedure

Ac2O (0.5 mL) was added into a solution of compound 34 (0.114 g, 0.24 mmol) in dry pyridine (4 mL). The reaction mixture was stirred at 20° C. for 3 h and then quenched by saturated aqueous NaHCO3 solution (2 mL). The organic phase was extracted with dichloromethane and then evaporated to dryness under reduced pressure. Purification by silica gel chromatography [petroleum ether:ethyl acetate (4:1)] afforded 35 (0.12 g, 88%) as a white solid. LC-MS: (M+H)+=517.2

Workup

customquenched by saturated aqueous NaHCO3 solution (2 mL)
extractionThe organic phase was extracted with dichloromethane
customevaporated to dryness under reduced pressure
customPurification by silica gel chromatography [petroleum ether:ethyl acetate (4:1)]

Sources & evidence

ORD record: ord-171eb1c8264748cfa0a082b7d911659e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09370569B2

Reaction notes

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