HCID 67619423, compound → L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide

HRID 2293393Notes

Reaction equation

HRID 2293393 reaction equation
C([O:8][C:9](=[O:34])[CH2:10][N:11]1[CH2:33][CH2:32][CH2:31][C@H:12]1[C:13]([N:15]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:16](=[O:23])[C@H:17]([C@H:19]([CH2:21][CH3:22])[CH3:20])[NH2:18])=[O:14])C1C=CC=CC=1.[H][H]>[Pd].CO>[C:9]([CH2:10][N:11]1[CH2:33][CH2:32][CH2:31][C@H:12]1[C:13]([N:15]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:16](=[O:23])[C@H:17]([C@H:19]([CH2:21][CH3:22])[CH3:20])[NH2:18])=[O:14])([OH:34])=[O:8]

Participants

5

Reactant 2

HCID 67619423HCID 67619423, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131720284L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamideYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
22 °C

Procedure

Using the hydrogenation conditions described in example 4, a solution of L-isoleucine, N-[1-(2-benzyloxy-2-oxoethyl)-L-prolyl] benzylamide (14.80 g, 31.76 mmol), 10% palladium on carbon (0.80 g), and methanol (350 mL), was purged with hydrogen, and stirred under an atmosphere of hydrogen at 22° C. After 8 hrs, the solution was purged with argon, filtered through a plug of celite, and concentrated in vacuo to provide 11.47 g, (96%) of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide as a white solid.

Workup

  1. customthe solution was purged with argon
  2. filtrationfiltered through a plug of celite
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9351814a98f049e6a400fbe1137ee82e
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

Loading…