2-Aminopyridine → N-alpha-t-BOC-L-phenylalanine 2-aminopyridine

HRID 1370690Notes

Reaction equation

[CH3:1][C:2]([O:5][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:7])([CH3:4])[CH3:3].[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C1CCC(N=C=NC2CCCCC2)CC1>>[CH3:4][C:2]([O:5][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:7])([CH3:1])[CH3:3].[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1

Participants

Reactant 3

HCID 104392-Aminopyridine

HCID 10868Dicyclohexylcarbodiimide

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 131722899N-alpha-t-BOC-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 a-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.

Sources & evidence

ORD record: ord-a9d0c88899e34b6cb87453beeed8f1bf
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06583191B2

Reaction notes

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