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

HRID 1448729Notes

Reaction equation

HRID 1448729 reaction equation
C(OC([NH:11][C@H:12]([C:14]([N:16]1[CH2:29][CH2:28][CH2:27][C@H:17]1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])=[O:15])[CH3:13])=O)C1C=CC=CC=1.CCOCC.[BrH:35]>C(O)(=O)C>[BrH:35].[NH2:11][C@H:12]([C:14]([N:16]1[CH2:29][CH2:28][CH2:27][C@H:17]1[C:18]([NH:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:19])=[O:15])[CH3:13]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 35369893HCID 35369893, compound

Product 1

HCID 22809936L-alanyl-L-proline anilide hydrobromideYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10 g (0.025 mol) of N-benzyloxycarbonyl-L-alanyl-L-proline anilide were dissolved in 50 ml of 4-N hydrogen bromide in acetic acid and the solution was stirred at room temperature for 1 hour. 300 ml of dry ether were then added. An oil precipitated out and was allowed to settle. The solution was decanted off and the oil was washed with two 150 ml portions of ether, dissolved in the minimum volume of methanol and treated with an excess of ethyl acetate. The product soon crystallised, there being obtained 7.2 g (83%) of L-alanyl-L-proline anilide hydrobromide of melting point 211°-214° C.

Workup

  1. customAn oil precipitated out
  2. customThe solution was decanted off
  3. washthe oil was washed with two 150 ml portions of ether
  4. dissolutiondissolved in the minimum volume of methanol
  5. additiontreated with an excess of ethyl acetate
  6. customThe product soon crystallised

Sources & evidence

ORD record
ord-fbf6324716904fcfaaf80f7025b051f8
Source dataset
uspto-grants-1980_02
Patent number
US04187216

Reaction notes

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