Hydrogen Bromide → HCID 86736707, compound

HRID 47040Notes

Reaction equation

HRID 47040 reaction equation
[CH2:1]([NH:3][C:4](=[O:23])[C@H:5]([CH3:22])[NH:6][C:7](=[O:21])[C@H:8]([CH3:20])[NH:9]C(OCC1C=CC=CC=1)=O)[CH3:2].[BrH:24].CCOCC>C(O)(=O)C>[BrH:24].[CH2:1]([NH:3][C:4](=[O:23])[C@H:5]([CH3:22])[NH:6][C:7](=[O:21])[C@H:8]([CH3:20])[NH2:9])[CH3:2]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 22216856N-Benzyloxycarbonyl-l-alanyl-l-alanine ethylamide

Product 1

HCID 86736707HCID 86736707, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7.5 g (0.023 mol) of N-benzyloxycarbonyl-L-alanyl-L-alanine ethylamide were stirred for 1 hour in 50 ml of 4-N hydrobromic acid in acetic acid. To the solution were added 300 ml of dry ether and, after stirring for a few minutes, the oil was allowed to settle and the ether decanted from the oil and discarded. The oil was then dissolved in methanol, the desired L-alanyl-L-alanine ethylamide hydrobromide crystallising out on the addition of ethyl acetate. The yield was 6.0 g (83%) and the melting point was 229°-231° C.; [α]D20 =-28.0° (c=1% in water).

Workup

  1. customthe ether decanted from the oil
  2. dissolutionThe oil was then dissolved in methanol
  3. additionthe desired L-alanyl-L-alanine ethylamide hydrobromide crystallising out on the addition of ethyl acetate
  4. custom[α]D20 =-28.0° (c=1% in water)

Sources & evidence

ORD record
ord-9d4890c47f4e4dc085f4c8c1496b3bc1
Source dataset
uspto-grants-1979_11
Patent number
US04176116

Reaction notes

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