Hydrogen Bromide → L-alanyl-L-proline cyclohexylamide hydrobromide

HRID 1448737Notes

Reaction equation

HRID 1448737 reaction equation
[CH:1]1([NH:7][C:8](=[O:29])[C@@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14](=[O:28])[C@H:15]([CH3:27])[NH:16]C(OCC2C=CC=CC=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCOCC.[BrH:35]>C(O)(=O)C>[BrH:35].[CH:1]1([NH:7][C:8](=[O:29])[C@@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14](=[O:28])[C@H:15]([CH3:27])[NH2:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 53880215HCID 53880215, compound

Product 1

HCID 70586840L-alanyl-L-proline cyclohexylamide hydrobromideYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2 g (0.005 mol) of N-benzyloxycarbonyl-L-alanyl-L-proline cyclohexylamide were dissolved in 10 ml of 4-N hydrogen bromide in acetic acid and the mixture was stirred at room temperature for 1 hour. 100 ml of dry ether were then added. An oil precipitated and was allowed to settle. The solution was decanted off, the oil washed with 100 ml of ether, dissolved in the minimum volume of methanol and an excess of ethyl acetate added. Crystallisation soon took place and there were obtained 1.75 g (100%) of L-alanyl-L-proline cyclohexylamide hydrobromide of melting point 233°-236° C.

Workup

  1. customAn oil precipitated
  2. customThe solution was decanted off
  3. washthe oil washed with 100 ml of ether
  4. dissolutiondissolved in the minimum volume of methanol
  5. additionan excess of ethyl acetate added
  6. customCrystallisation soon took place

Sources & evidence

ORD record
ord-9077db9f20ed48fe81c39a06633bca84
Source dataset
uspto-grants-1980_02
Patent number
US04187216

Reaction notes

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