Diisopropylethylamine → (S)-tert-butyl 6-(bis((1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)-2-(3-((S)-1-tert-butoxy-1,5-dioxo-5-(4-sulfamoylphenethylamino)pentan-2-yl)ureido)hexanoate

HRID 56324

Reaktionsgleichung

Reaktionsgleichung von HRID 56324
[C:1]([O:5][C:6](=[O:58])[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][N:14]([CH2:44][C:45]1[N:46]([CH2:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])[CH:47]=[CH:48][N:49]=1)[CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]([NH:27][C:28](=[O:43])[NH:29][C@H:30]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:31][CH2:32][C:33](O)=[O:34])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([CH3:4])([CH3:3])[CH3:2].[NH2:59][CH2:60][CH2:61][C:62]1[CH:67]=[CH:66][C:65]([S:68]([NH2:71])(=[O:70])=[O:69])=[CH:64][CH:63]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:53]([O:52][C:51](=[O:57])[CH2:50][N:46]1[CH:47]=[CH:48][N:49]=[C:45]1[CH2:44][N:14]([CH2:13][C:9]1[N:8]([CH2:7][C:6](=[O:58])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:12]=[CH:11][N:10]=1)[CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]([NH:27][C:28]([NH:29][C@@H:30]([CH2:31][CH2:32][C:33](=[O:34])[NH:59][CH2:60][CH2:61][C:62]1[CH:63]=[CH:64][C:65]([S:68](=[O:69])(=[O:70])[NH2:71])=[CH:66][CH:67]=1)[C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])=[O:43])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([CH3:54])([CH3:55])[CH3:56]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 59404337(S)-4-(3-((S)-6-(bis((1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)-1-tert-butoxy-1-oxohexan-2-yl)ureido)-5-tert-butoxy-5-oxopentanoic acid

Produkt 1

HCID 86762744(S)-tert-butyl 6-(bis((1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)-2-(3-((S)-1-tert-butoxy-1,5-dioxo-5-(4-sulfamoylphenethylamino)pentan-2-yl)ureido)hexanoateAusbeute 101,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (S)-4-(3-((S)-6-(bis((1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)-1-tert-butoxy-1-oxohexan-2-yl)ureido)-5-tert-butoxy-5-oxopentanoic acid (80 mg, 0.098 mmol), 4-(2-aminoethyl)benzenesulfonamide (30 mg, 0.15 mmol), 2-(1-H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU, 50 mg, 0.17 mmol), and DIPEA (0.50 mL) in DMF (5 mL) was stirred at 40° C. overnight. The solvents were evaporated under reduced pressure to give a residue, which was purified by Biotage SP4 using a gradient of 0-20% MeOH in DCM to give (S)-tert-butyl 6-(bis((1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)-2-(3-((S)-1-tert-butoxy-1,5-dioxo-5-(4-sulfamoylphenethylamino)pentan-2-yl)ureido)hexanoate (100 mg, 100%). ESMS m/z: 501.9 (M/2+H)+.

Aufarbeitung

  1. customThe solvents were evaporated under reduced pressure
  2. customto give a residue, which
  3. customwas purified by Biotage SP4

Quellen und Nachweise

ORD-Eintrag
ord-fa99c03efb2942e7927744fc846d49ed
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09433594B2

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