Decanoic Acid → N-alpha-decyl-L-phenylalanine 2-aminopyridine

Reaction equation

CC(O[C:6]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)(C)C.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.[C:27](O)(=O)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]C.C1CCC(N=C=NC2CCCCC2)CC1>>[CH2:6]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1

Participants

Reactant 3

HCID 2969Decanoic Acid

HCID 10868Dicyclohexylcarbodiimide

HCID 131722899N-alpha-t-BOC-L-phenylalanine 2-aminopyridine

Product 1

HCID 69929295N-alpha-decyl-L-phenylalanine 2-aminopyridine

Procedure

The acylated phenylalanine anilide imprint molecule was synthesized in three steps. (1) N-α-t-BOC-L-phenylalanine was coupled with 2-aminopyridine using DCC to give N-α-t-BOC-L-phenylalanine-2-aminopyridine. (2) The α-amine was then deprotected with TFA to give N-α-L-phenylalanine-2-aminopyridine. (3) To create a compound having the properties of a surfactant, the free amine was then acylated with decanoic acid using DCC to give N-α-decyl-L-phenylalanine-2-aminopyridine.