Diethyl Ether → L-alanyl-L-proline n-pentylamide

HRID 1448745Notes

Reaction equation

HRID 1448745 reaction equation
[CH2:1]([NH:6][C:7](=[O:28])[C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:27])[C@H:14]([CH3:26])[NH:15]C(OCC1C=CC=CC=1)=O)[CH2:2][CH2:3][CH2:4][CH3:5].CCOCC>Br.C(O)(=O)C>[CH2:1]([NH:6][C:7](=[O:28])[C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:27])[C@H:14]([CH3:26])[NH2:15])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 53667817HCID 53667817, compound

Product 1

HCID 54383360L-alanyl-L-proline n-pentylamideYield 152.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

2.5 g of N-benzyloxycarbonyl-L-alanyl-L-proline n-pentylamide were dissolved in 15 ml of 4-N hydrogen bromide in acetic acid and the solution was stirred for 1 hour at room temperature. 150 ml of dry ether were added. An oil precipitated out and was allowed to settle. The ether was decanted off and the procedure repeated using 150 ml of fresh ether. On evaporation there were obtained 2.5 g of L-alanyl-L-proline n-pentylamide in the form of a white solid.

Workup

  1. customAn oil precipitated out
  2. customThe ether was decanted off
  3. customOn evaporation there

Sources & evidence

ORD record
ord-f1c080d621b844b1b64286a577ad7823
Source dataset
uspto-grants-1980_02
Patent number
US04187216

Reaction notes

Loading…