methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-phenylbutanoate → Boc-homophenylalaninal
Reaction equation
C[O:2][C:3](=O)[C@H:4]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>C1(C)C=CC=CC=1>[C:6]([NH:5][C@H:4]([CH:3]=[O:2])[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:7]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -80 °C
Procedure
2.93 g of N-BOC homo phenylalanine methyl ester (10 mmol) are dissolved in 25 ml of absolute toluene under nitrogen and the solution is cooled to -80° C. 20 ml of -20% strength DIBA in toluene are added dropwise and the temperature maintained. Since the reaction was not complete after 1.5 h a further 3 ml of 20% strength DIBA were added.