Hydrochloric Acid → HCID 178479664, compound

HRID 1650169Notes

Reaction equation

HRID 1650169 reaction equation
C(OC[CH:10]([OH:23])[CH:11]([CH2:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1)[C:12]([O:14][CH2:15]C)=[O:13])C1C=CC=CC=1.[ClH:24]>C(O)C.[Pd]>[ClH:24].[OH:23][CH:10]1[CH2:15][O:14][C:12](=[O:13])[CH:11]1[CH2:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178471158HCID 178471158, compound

Product 1

HCID 178479664HCID 178479664, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

93.9 g (0.295 mole) of ethyl 4-benzyloxy-3-hydroxy-2-[(1H-imidazol-4-yl)methyl]-butanoate dissolved in 500 ml of absolute ethanol and 65 ml of a 6.8N ethanolic solution of hydrochloric acid, are subjected to hydrogenolysis in the presence of 5 g of 10% palladium on carbon under a hydrogen pressure of 3.5 bars. The catalyst is then filtered off and the solvent is eliminated at 65° C. under reduced pressure. 67.1 g of 4-hydroxy-3-[(1H-imidazol-4-yl)methyl]-dihydro-2(3H)-furanone hydrochloride are obtained (mixture of diastereoisomers). Practically quantitative yield. The product obtained is used as such in the following step.

Workup

  1. filtrationThe catalyst is then filtered off
  2. customis eliminated at 65° C. under reduced pressure

Sources & evidence

ORD record
ord-c59a198f0434483c8f526643b083ab94
Source dataset
uspto-grants-1990_05
Patent number
US04923865

Reaction notes

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