Isopropanol hydrochloride → HCID 22821028, compound

HRID 1759383Notes

Reaction equation

HRID 1759383 reaction equation
C(OC([NH:11][C@H:12]([C:16]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[C:31]([F:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:22][C@@H:21]1[OH:34])=[O:17])[CH:13]([CH3:15])[CH3:14])=O)C1C=CC=CC=1.[ClH:35].C(O)(C)C.[H][H]>C(O)(C)C.[C].[Pd]>[ClH:35].[NH2:11][C@H:12]([C:16]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[C:31]([F:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:22][C@@H:21]1[OH:34])=[O:17])[CH:13]([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 21912024Isopropanol hydrochlorideHCID 22821017HCID 22821017, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22821028HCID 22821028, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of 1.70 g (3.55 m-mol) of 5'-O-(N-benzyloxycarbonylvalyl)-2'-deoxy-5-fluorouridine obtained in Example 26 in 50 ml of isopropyl alcohol were added 10% palladium-carbon (750 mg) and a solution of 16.0% hydrogen chloride-isopropyl alcohol (810 mg). The mixture was stirred for 3.5 hours in a stream of hydrogen under normal pressure at ordinary temperature. The catalyst was filtered off and the solvent was distilled off under reduced pressure from the reaction mixture and the residue was dissolved in isopropyl alcohol (5 ml). A small amount of ether was added to this solution and the resultant white precipitate was collected by filtration in a stream of dry nitrogen whereby 1.14 g (yield: 84.1%) of 5'-O-(valyl)-2'-deoxy-5-fluorouridine hydrochloride was obtained.

Workup

  1. filtrationThe catalyst was filtered off
  2. distillationthe solvent was distilled off under reduced pressure from the reaction mixture
  3. dissolutionthe residue was dissolved in isopropyl alcohol (5 ml)
  4. additionA small amount of ether was added to this solution

Sources & evidence

ORD record
ord-b039be96df9e4946846fd7d0cd0c5d40
Source dataset
uspto-grants-1982_07
Patent number
US04340728

Reaction notes

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