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

HRID 47043Notes

Reaction equation

[CH2:1]([NH:3][C:4](=[O:25])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:24])[C@H:11]([CH3:23])[NH:12]C(OCC1C=CC=CC=1)=O)[CH3:2].[BrH:26].CCOCC>C(O)(=O)C>[BrH:26].[CH2:1]([NH:3][C:4](=[O:25])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:24])[C@H:11]([CH3:23])[NH2:12])[CH3:2]

Participants

Conditions

Temperature: -60 °C

Procedure

1.81 g (0.0052 mol) of N-benzyloxycarbonyl-L-alanyl-L-proline ethylamide were stirred for 1 hour in 10 ml of 4-N hydrobromic acid in acetic acid. To the solution were added 150 ml of dry ether and, after stirring for a few minutes, the oil was allowed to settle. The mixture was cooled to -60° C. and the ether decanted from the oil and discarded. The oil was then dissolved in methanol, the product crystallising out on the addition of ethyl acetate. There were obtained 1.25 g (82%) of L-alanyl-L-proline ethylamide hydrobromide of melting point 202°-204° C.

Workup

customthe ether decanted from the oil
dissolutionThe oil was then dissolved in methanol
customthe product crystallising out on the addition of ethyl acetate

Sources & evidence

ORD record: ord-83dee15e6ad243779612f1005e1fd9b0
Source dataset: uspto-grants-1979_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04176116

Reaction notes

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