Diisopropylethylamine → N1-{(1S,2R)-1-Benzyl-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-N3-methyl-5-(1,3-oxazol-2-yl)-N3-propylisophthalamide

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Edukt	N-Methyl-5-oxazol-2-yl-N-propyl-isophthalamic acid	HCID 21085840	—
Edukt	(2R,3S)-3-amino-1-[(3-ethylbenzyl)amino]-4-phenylbutan-2-ol dihydrochloride	HCID 57487283	—
Lösungsmittel	Dimethylformamide	HCID 6228	—
Produkt	N1-{(1S,2R)-1-Benzyl-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-N3-methyl-5-(1,3-oxazol-2-yl)-N3-propylisophthalamide	HCID 58802665	—

Reaktionsschritte

To 3-{[methyl(propyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoic acid (206 mg, 0.71 mmol) in DMF (5 mL) is added diisopropylethylamine (174 μL, 1.1 mmol), HATU (323 mg, 0.85 mmol), then (2R,3S)-3-amino-1-[(3-ethylbenzyl)amino]-4-phenylbutan-2-ol dihydrochloride prepared by the method of Example SP-272 (292 mg, 0.79 mmol). The reaction is stirred 4 h at room temperature. The reaction is partitioned between chloroform and water. The organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 8% methanol/chloroform) gives the title compound. ESI MS m/z 569.3 [M+H]+.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US07727997B2
Quelldatensatz	uspto-grants-2010_06
ORD ID	ord-aaf20ede3f774b73bf97db86b6d80b00
Quellennotiz	uspto-grants-2010_06