Hydrochloric Acid → 4hydroxy-L-proline ethyl ester hydrochloride

HRID 1583931Notes

Reaction equation

HRID 1583931 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C@@H:5]1[CH2:9][CH:8]([OH:10])[CH2:7][N:6]1C(OCC1C=CC=CC=1)=O)[CH3:2].[ClH:22]>C(O)C.[Pd]>[ClH:22].[CH2:1]([O:3][C:4](=[O:21])[C@@H:5]1[CH2:9][CH:8]([OH:10])[CH2:7][NH:6]1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18600533N-Cbz-4-hydroxy-L-proline ethyl ester

Product 1

HCID 127093054hydroxy-L-proline ethyl ester hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of N-Cbz-4-hydroxy-L-proline ethyl ester (3.29 g) in 40 ml ethanol was added 6 ml of ethanol saturated with gaseous HCl followed by 10% palladium on carbon (0.50 g). The mixture was hydrogenated on a Parr Hydrogenator at 30-40 psi for 3 hours. The solution was filtered over celite and concentrated in vacuo to provide 2.09 g of the crystalline product.

Workup

  1. filtrationThe solution was filtered over celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df2c37ad716a4685b353dc050e3e951c
Source dataset
uspto-grants-1985_11
Patent number
US04555508

Reaction notes

Loading…