Diisopropylethylamine → (S)-methyl 13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oate

HRID 62710

Reaktionsgleichung

Reaktionsgleichung von HRID 62710
Cl.[NH2:2][C@@H:3]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:4]([NH:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:5].[C:16]([O:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](O)=[O:30])=[O:22])([CH3:19])([CH3:18])[CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1>[CH2:12]([C@@H:3]([C:4](=[O:5])[NH:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])[NH:2][C:29](=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][NH:23][C:21](=[O:22])[O:20][C:16]([CH3:17])([CH3:18])[CH3:19])[CH:13]([CH3:15])[CH3:14]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18603049(S)-methyl 2-(2-amino-4-methylpentanamido)acetate hydrochloride

Produkt 1

HCID 86712539(S)-methyl 13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (S)-methyl 2-(2-amino-4-methylpentanamido)acetate hydrochloride (4w) in THF was added 6-((tert-butoxycarbonyl)amino) hexanoic acid, HATU and DIPEA. The reaction was stirred at room temperature for 18 h. The mixture was then filtered through Celite. The filtrate was concentrated under reduced pressure and the crude residue was purified by column chromatography (silica gel, CH2Cl2/MeOH=50/1) to give (S)-methyl 13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oate (6w) as a white solid.

Aufarbeitung

  1. filtrationThe mixture was then filtered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe crude residue was purified by column chromatography (silica gel, CH2Cl2/MeOH=50/1)

Quellen und Nachweise

ORD-Eintrag
ord-4ed965af7e3446378ee425ce7b7a758d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447030B2

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