Hydrogen Bromide → HCID 22809933, compound

HRID 1448723Notes

Reaction equation

HRID 1448723 reaction equation
C(OC([N:11]([C:18](=[O:22])[C@H:19]([CH3:21])[NH2:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)C1C=CC=CC=1.CCOCC.[BrH:28]>C(O)(=O)C>[BrH:28].[NH2:20][C@H:19]([C:18]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 22843586HCID 22843586, compound

Product 1

HCID 22809933HCID 22809933, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6 g (0.02 mol) of N-benzyloxycarbonyl-L-alanine anilide were dissolved in 30 ml of 4-N hydrogen bromide in acetic acid and the solution was stirred for 1 hour at room temperature. 300 ml of dry ether were then added. An oil precipitated out and was allowed to settle. The solvents were decanted off and the oil was washed with two 150 ml portions of ether, dissolved in a small amount of methanol and an excess of ethyl acetate was added. The product crystallised out, there being obtained 4.0 g (81%) of L-alanine anilide hydrobromide of melting point 244°-247° C.

Workup

  1. customAn oil precipitated out
  2. customThe solvents were decanted off
  3. washthe oil was washed with two 150 ml portions of ether
  4. dissolutiondissolved in a small amount of methanol
  5. additionan excess of ethyl acetate was added
  6. customThe product crystallised out

Sources & evidence

ORD record
ord-601f1fe595a54b7eb7ae05ea02a5be9a
Source dataset
uspto-grants-1980_02
Patent number
US04187216

Reaction notes

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