HCID 131712543, compound → 5-Oxo-L-prolyl-L-leucyl-N-decyl-L-prolinamide

HRID 1155086Notes

Reaction equation

HRID 1155086 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]([N:17]1[CH2:34][CH2:33][CH2:32][C@H:18]1[C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8]>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]([N:17]1[CH2:34][CH2:33][CH2:32][C@H:18]1[C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8]

Participants

4

Reactant 1

HCID 131712543HCID 131712543, compound

Product 1

HCID 133125275-Oxo-L-prolyl-L-leucyl-N-decyl-L-prolinamideYield 77.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.22 g (2 mmoles) of Z-Glp-Leu-Pro-NH-C10H21 are dissolved in 30 ml of methanol, 0.2 g of a 10% palladium-on-carbon catalyst are added, and hydrogen is bubbled through the mixture for 30 minutes. The catalyst is filtered off, the filtrate is evaporated, and the oily residue is crystallized from n-hexane. The resulting 0.85 g of crude product are recrystallized from 4 ml of ethyl acetate to obtain 0.74 g (77%) of Glp-Leu-Pro-NH-C10H21 ; m.p.: 140°-141° C., Rf4 =0.76, [α]D25 =-71.3° (c=1%, in acetic acid). Amino acid analysis: Glu: 0.97 (1.0), Leu: 1.00 (1.0), Pro: 1.01 (1.0).

Workup

  1. customhydrogen is bubbled through the mixture for 30 minutes
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customthe oily residue is crystallized from n-hexane
  5. customThe resulting 0.85 g of crude product are recrystallized from 4 ml of ethyl acetate

Sources & evidence

ORD record
ord-4e7993ed7b194611af20d6fbb177b8ca
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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