Diisopropylethylamine → HCID 178459155, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-Carboxy-1,2,3-triazole	HCID 140120	—
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	(2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid oxetan-3-yl ester	HCID 68181152	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 178459155	HCID 178459155	15.1%

Reaction Steps

1,2,3-Triazole-4-carboxylic acid (0.0274 g, 0.242 mmol), DIPEA (169 μL, 969 μmol) and HATU (92 mg, 242 μmol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid oxetan-3-yl ester (89.5 mg, 242 μmol), predissolved in DMF (0.2 mL) and DIPEA (0.5 eq.). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The product was purified by preparative HPLC and lyophilized to yield the title compound (17 mg; purity 95%). MS m/z [M+H]+ calc'd for C25H28N4O5, 465.21. found 465.4.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08481044B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-f0bc0b0e2a3641d6babb4f92e4c38b3b
Source note	uspto-grants-2013_07