Ethanol hydrochloride → 5'-O-{N-(N-lysylalanyl)isoleucyl}-5-fluorouridine dihydrochloride
Reaction equation
C(OC([NH:11][C@H:12]([C:28]([NH:30][C@H:31]([C:33]([NH:35][C@H:36]([C:41]([O:43][CH2:44][C@H:45]1[O:49][C@@H:48]([N:50]2[CH:57]=[C:56]([F:58])[C:54](=[O:55])[NH:53][C:51]2=[O:52])[C@H:47]([OH:59])[C@@H:46]1[OH:60])=[O:42])[C@H:37]([CH2:39][CH3:40])[CH3:38])=[O:34])[CH3:32])=[O:29])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17]C(OCC1C=CC=CC=1)=O)=O)C1C=CC=CC=1.[ClH:61].C(O)C.[H][H]>C(O)C.CO.[C].[Pd]>[ClH:61].[ClH:61].[NH2:11][C@H:12]([C:28]([NH:30][C@H:31]([C:33]([NH:35][C@H:36]([C:41]([O:43][CH2:44][C@H:45]1[O:49][C@@H:48]([N:50]2[CH:57]=[C:56]([F:58])[C:54](=[O:55])[NH:53][C:51]2=[O:52])[C@H:47]([OH:59])[C@@H:46]1[OH:60])=[O:42])[C@H:37]([CH2:39][CH3:40])[CH3:38])=[O:34])[CH3:32])=[O:29])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
0.94 Gram (1.11 mmol) of the ester obtained as described above was dissolved in ethanol (100 ml) and methanol (20 ml), and 0.40 g of 10% palladium-carbon and 0.50 g (4.93 mmol) of 36% hydrogen chloride-ethanol were added. The mixture was stirred in a stream of hydrogen under normal pressure for 2 hours at room temperature. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was washed with ether (20 ml) to obtain 0.71 g (99%) of the desired 5'-O-{N-(N-lysylalanyl)isoleucyl}-5-fluorouridine dihydrochloride as a colorless powdery solid.
Workup
- filtrationThe catalyst was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- washThe residue was washed with ether (20 ml)
Sources & evidence
- ORD record
- ord-a684b95c5bfc41e9adf65dff0b86e3b3
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04892939
Reaction notes
Loading…