4-Aminopyridine → (2S)-2-[isobutyl(p-tolylsulfonyl)amino]-6-[[2-(4-pyridylamino)acetyl]amino]hexanoic acid

HRID 396919

Reaction equation

[CH2:1]([N:5]([S:19]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)(=[O:21])=[O:20])[C@H:6]([C:16]([OH:18])=[O:17])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:15])[CH2:13]I)[CH:2]([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.[NH2:38][C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1>>[CH3:28][C:25]1[CH:26]=[CH:27][C:22]([S:19]([N:5]([C@H:6]([C:16]([OH:18])=[O:17])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([CH2:13][NH:38][C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)=[O:15])[CH2:1][CH:2]([CH3:4])[CH3:3])(=[O:21])=[O:20])=[CH:23][CH:24]=1

Participants

Reactant 3

HCID 17274-Aminopyridine

HCID 81531Diisopropylethylamine

HCID 86589941Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-Nepsilon-iodoacetyl-L-lysine

Product 1

HCID 508634(2S)-2-[isobutyl(p-tolylsulfonyl)amino]-6-[[2-(4-pyridylamino)acetyl]amino]hexanoic acid

Procedure

The title compound was prepared from Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-Nε-iodoacetyl-L-lysine (150 mg, 0.29 mmol, example 105, step B) by following the indications of general procedure H using DIEA (0.10 mL, 0.57 mmol) and 4-aminopyridine (76 mg, 0.59 mmol). The crude material was purified by preparative HPLC. The product was isolated as a solid (39 mg, 28% yield).

Workup

customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record: ord-ddcbdcdedd8143b59b3d4e99db9e2c31
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608100B1

Linked notes

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