Acetic Acid → HCID 86638038, compound
Reaction equation
C(N[C:10]1[CH:41]=[CH:40][N:13]([C@@H:14]2[O:29][C@H:18]([CH:19]([C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[OH:20])[C@@:16]([C:30](=[O:37])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([OH:17])[C@:15]2([F:39])[CH3:38])[C:12](=[O:42])[N:11]=1)(=O)C1C=CC=CC=1.CC(O)=[O:45]>>[C:30]([C@@:16]1([OH:17])[C@@H:18]([CH:19]([C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[OH:20])[O:29][C@@H:14]([N:13]2[CH:40]=[CH:41][C:10](=[O:45])[NH:11][C:12]2=[O:42])[C@@:15]1([F:39])[CH3:38])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1Participants
3
Procedure
N4,3′,5′-tribenzoyl-2′-Deoxy-2′-fluoro-2′-C-methylcytidine (2.0 g, 1 eq) was refluxed in 80% aqueous AcOH overnight. After cooling and standing at room temperature (15° C.), most of the product precipitated and then was filtered through a sintered funnel. White precipitate was washed with water and co-evaporated with toluene to give a white solid. The filtrate was concentrated and co-evaporated with toluene to give additional product which was washed with water to give a white solid. Combining the two batches of white solid gave 1.50 g of 3′,5′-dibenzoyl-2′-Deoxy-2′-fluoro-2′-C-methyluridine (Yield: 91%).
Workup
- temperatureAfter cooling
- customstanding at room temperature
- custom(15° C.)
- custommost of the product precipitated
- filtrationwas filtered through a sintered funnel
- washWhite precipitate was washed with water and co-evaporated with toluene
- customto give a white solid
- concentrationThe filtrate was concentrated
- customto give additional product which
- washwas washed with water
- customto give a white solid
Sources & evidence
- ORD record
- ord-44897f1fd2234df19d8bf7b1dfb6e5b5
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906880B2
Reaction notes
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