Diisopropylethylamine → HCID 86762441, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	HCID 66771102	HCID 66771102	—
Reactant	(2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide dihydrochloride	HCID 86762404	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 86762441	HCID 86762441	—

Reaction Steps

(2S,4R)-1-(tert-butoxycarbonyl)-4-(2,4-dimethylphenylsulfonyl)pyrrolidine-2-carboxylic acid (120 mg, 313 μmol, Eq: 1.00, prepared as described in U.S. Pat. Appl. US20100267722), (2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide dihydrochloride (99.7 mg, 407 μmol, Eq: 1.3), N,N-diisopropylethylamine (121 mg, 164 μA, 939 μmol, Eq: 3) and HATU (202 mg, 532 μmol, Eq: 1.7) were combined with DMF (2 ml) to give a light brown solution. The reaction was stirred overnight at RT. The crude material was purified by preparative HPLC (column: ymc C18 (120 A), 75×30 mm, acetonitrile/water (+0.1% formic acid)=95%-5% to 5%-95% in 8 min, flow: 25 ml/min). After evaporation of solvents, the title compound was obtained as a light brown foam (64.3 mg, 38.2%, MS (m/e)=538.3 [M+H+]).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08729061B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-436a9d74c85f4792863bc172de5583de
Source note	uspto-grants-2014_05