HCID 131713004, compound → HCID 131713003, compound

HRID 851726Notes

Reaction equation

HRID 851726 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:15]([OH:17])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8].[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1.[H][H]>CO.[Pd]>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:15]([OH:17])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8].[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 2

HCID 131713004HCID 131713004, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131713003HCID 131713003, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.0 g (4.66 mmoles) of Z-Glp-Leu-pyrrolidine are dissolved in 40 ml of methanol, 0.4 g of a 10% palladium-on-carbon catalyst are added to the solution, and hydrogen is bubbled through the mixture for one hour. The catalyst is filtered off, the filtrate is evaporated, the oily residue is dissolved in ether, and the solution is allowed to stand at a cool place overnight. The separated crystals are filtered off to obtain 1.25 g (91%) of Glp-Leu-pyrrolidine; m.p.: 103°-104° C., Rf5 =0.65, [α]D25 =-31.6° (c=1%, in acetic acid). Analysis for amino acids: Glu=1.00 (1.0), Leu=1.00 (1.0).

Workup

  1. customis bubbled through the mixture for one hour
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. dissolutionthe oily residue is dissolved in ether
  5. customto stand at a cool place overnight
  6. filtrationThe separated crystals are filtered off

Sources & evidence

ORD record
ord-d6b5cff635ae43c49ff8fd00a3302e6f
Source dataset
uspto-grants-1983_05
Patent number
US04386073

Reaction notes

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