Pivaloyl chloride → N-pivaloyl-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].[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>N1C=CC=CC=1>[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:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1 g (0.0033 mol) of L-alanyl-L-proline ethylamide hydrobromide was dissolved in 20 ml of dry pyridine and 0.45 ml of pivaloyl chloride was added. The mixture was stirred for 1 hour at room temperature and then the pyridine was removed by evaporation. The oil was triturated with toluene, re-evaporated and then partitioned between chloroform and saturated brine. The chloroform layer was separated and dried over magnesium sulphate, filtered off and evaporated to a clear oil which crystallised on the addition of petrol. The solid was filtered off, washed with petrol and dried to yield 0.4 g (40%) of N-pivaloyl-L-alanyl-L-proline ethylamide of melting point 94°-96° C.
Workup
- customthe pyridine was removed by evaporation
- customThe oil was triturated with toluene
- customre-evaporated
- custompartitioned between chloroform and saturated brine
- customThe chloroform layer was separated
- dry with materialdried over magnesium sulphate
- filtrationfiltered off
- customevaporated to a clear oil which
- customcrystallised on the addition of petrol
- filtrationThe solid was filtered off
- washwashed with petrol
- customdried
Sources & evidence
- ORD record
- ord-44e9d2b1f1b34b568821915aaefdf744
- Source dataset
- uspto-grants-1979_11
- Patent number
- US04176116
Reaction notes
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