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

HRID 431348

Reaction equation

HRID 431348 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.[NH:38]([C:45]1[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=1)C1C=CC=CC=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:45]2[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=2)=[O:15])[CH2:1][CH:2]([CH3:4])[CH3:3])(=[O:21])=[O:20])=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 89945N-phenylpyridin-4-amineHCID 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-amiinopyridine (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

  1. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-d8b4a70dc5ca423d9ea7f6c74551a935
Source dataset
uspto-grants-2003_12
Patent number
US06656965B2

Linked notes

Loading…