Aniline → HCID 22843586, compound
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14](O)=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:19]1[CH2:24][CH2:23][O:22]CC1)C.ClC(O[CH2:29][CH:30](C)[CH3:31])=O.N[C:34]1C=CC=CC=1>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]([C:23](=[O:22])[C@H:24]([CH3:34])[NH2:19])[C:12]1[CH:13]=[CH:31][CH:30]=[CH:29][CH:14]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
11.15 g (0.05 mol) of N-benzyloxycarbonyl-L-alanine were dissolved in 75 ml of dry tetrahydrofuran and the mixture was cooled to -10° C. 6.35 ml (0.05 mol) of N-ethylmorpholine were added followed by 6.5 ml of isobutyl chloroformate and the resulting solution was stirred at -10° C. for 20 minutes. 4.65 ml (0.05 mol) of aniline were then added, the mixture was stirred at 0° C. for 1 hour and then left to stand at room temperature for 3 hours. The solvents were removed by evaporation and the residue was dissolved in 200 ml of chloroform. The solution was washed with 150 ml of 1-N hydrochloric acid, 150 ml of water and 150 ml of 5% sodium bicarbonate solution, dried over magnesium sulphate and evaporated to give a white solid. This solid was treated with 300 ml of petroleum ether to yield 11.89 g (80%) of N-benzyloxycarbonyl-L-alanine anilide of melting point 161°-163° C.
Workup
- stirringthe mixture was stirred at 0° C. for 1 hour
- waitleft
- waitto stand at room temperature for 3 hours
- customThe solvents were removed by evaporation
- dissolutionthe residue was dissolved in 200 ml of chloroform
- washThe solution was washed with 150 ml of 1-N hydrochloric acid, 150 ml of water and 150 ml of 5% sodium bicarbonate solution
- dry with materialdried over magnesium sulphate
- customevaporated
- customto give a white solid
Sources & evidence
- ORD record
- ord-90acc356e63a48ea84d1d462fad87afe
- Source dataset
- uspto-grants-1980_02
- Patent number
- US04187216
Reaction notes
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