Diethyl Ether → HCID 22691450, compound

HRID 1448744Notes

Reaction equation

HRID 1448744 reaction equation
[CH2:1]([NH:6][C:7](=[O:23])[C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1C(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:23])[C@@H:8]1[CH2:12][CH2:11][CH2:10][NH:9]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 54292613HCID 54292613, compound

Product 1

HCID 22691450HCID 22691450, compoundYield 117.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

5 g of N-benzyloxycarbonyl-L-proline n-pentylamide were dissolved in 20 ml of 4-N hydrogen bromide in acetic acid and the mixture was stirred for 1 hour. 150 ml of dry ether were then added. A clear oil precipitated out and was allowed to settle. The ether was decanted off and the oil washed with a further 100 ml of dry ether. Evaporation yielded 3.4 g (82%) of L-proline n-pentylamide in the form of an oil.

Workup

  1. customA clear oil precipitated out
  2. customThe ether was decanted off
  3. washthe oil washed with a further 100 ml of dry ether
  4. customEvaporation

Sources & evidence

ORD record
ord-590edca276d14149b4386ac267e1ddde
Source dataset
uspto-grants-1980_02
Patent number
US04187216

Reaction notes

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