Hydrogen Bromide → HCID 22809934, compound

HRID 1448724Notes

Reaction equation

HRID 1448724 reaction equation
C(OC([NH:11][C@H:12]([C:14]([NH:16][C@H:17]([C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20])[CH3:18])=[O:15])[CH3:13])=O)C1C=CC=CC=1.CCOCC.[BrH:33]>C(O)(=O)C>[BrH:33].[NH2:11][C@H:12]([C:14]([NH:16][C@H:17]([C:19]([NH:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:20])[CH3:18])=[O:15])[CH3:13]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 54205079HCID 54205079, compound

Product 1

HCID 22809934HCID 22809934, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5.5 g (0.0149 g) of N-benzyloxycarbonyl-L-alanyl-L-alanine anilide were dissolved in 30 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. A white solid separated out and was allowed to settle. The solution was decanted off and the solid washed with two 150 ml portions of ether. Recrystallisation of the solid from methanol/ethyl acetate yielded 4.1 g (88%) of L-alanyl-L-alanine anilide hydrobromide.

Workup

  1. customA white solid separated out
  2. customThe solution was decanted off
  3. washthe solid washed with two 150 ml portions of ether
  4. customRecrystallisation of the solid from methanol/ethyl acetate

Sources & evidence

ORD record
ord-1c490e5d3f2e4c579cd5d9723d7a0f7f
Source dataset
uspto-grants-1980_02
Patent number
US04187216

Reaction notes

Loading…