Benzoyl chloride → N-benzoyl-L-alanyl-L-proline ethylamide
Reaction equation
Br.[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH2:13])[CH3:3].[OH-].[Na+].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH:13][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1.42 g (0.0048 mol) of L-alanyl-L-proline ethylamide hydrobromide were dissolved in 20 ml of methylene chloride, 21.8 ml (0.01 mol) of 0.5-N sodium hydroxide solution were added followed by 0.54 ml (0.0053 mol) of benzoyl chloride. The mixture was stirred vigorously at room temperature for 1 hour with care being taken that the solution remained basic, this being achieved by the addition of a few drops of 0.5-N sodium hydroxide solution. The layers were then allowed to separate and the methylene chloride layer was separated, dried over magnesium sulphate and evaporated to an oil which crystallised on treatment with ethyl acetate. The crystals were filtered off, washed and dried to yield 1.05 g of N-benzoyl-L-alanyl-L-proline ethylamide of melting point 200°-202° C.; [α]D20 =-82.7° (c=0.99 in methanol).
Workup
- customto separate
- customthe methylene chloride layer was separated
- dry with materialdried over magnesium sulphate
- customevaporated to an oil which
- customcrystallised on treatment with ethyl acetate
- filtrationThe crystals were filtered off
- washwashed
- customdried
Sources & evidence
- ORD record
- ord-00cb2a1f19a44f2d8f439eb07dc5a70f
- Source dataset
- uspto-grants-1979_11
- Patent number
- US04176116
Reaction notes
Loading…