HCID 86751514, compound → HCID 86751513, compound

HRID 2293344Notes

Reaction equation

HRID 2293344 reaction equation
C([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O.[CH2:19]([NH:26][C:27](=[O:34])[C@H:28]([C@H:30]([CH2:32][CH3:33])[CH3:31])[NH2:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>[Pd].CO>[NH:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14].[CH2:19]([NH:26][C:27](=[O:34])[C@H:28]([C@H:30]([CH2:32][CH3:33])[CH3:31])[NH2:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 86751514HCID 86751514, compound

Product 1

HCID 86751513HCID 86751513, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
22 °C

Procedure

A solution of N-carbobenzyloxy-L-proline-L-isoleucine benzylamide (36.60 g, 80.95 mmol), 10% palladium on carbon (0.957 g), and methanol (700 mL) was degassed and purged repeatedly (15 times) with hydrogen, and stirred under an atmosphere of hydrogen at 22° C. When TLC analysis indicated the reaction was complete, the solution was purged with argon, filtered through a plug of celite, and concentrated in vacuo to provide 23.71 g, (92%) of L-proline-L-isoleucine benzylamide as a white solid.

Workup

  1. custompurged repeatedly (15 times) with hydrogen
  2. customthe solution was purged with argon
  3. filtrationfiltered through a plug of celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-975a2f6764c24cf18bea9d718b77f394
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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