Diisopropylethylamine → HCID 67410996, compound

https://huagongshe.com/reaction/1949650

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Boc-L-Valine	HCID 83693	—
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 67408499	HCID 67408499	—
Solvent	Diethyl Ether	HCID 3283	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	HCID 67410996	HCID 67410996	87.4%

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a solution containing Boc-Val-OH (106 mg, 0.48 mmol) in anhydrous NMP (3 mL) was cooled to 0° C. HATU (185 mg, 0.48 mmol) and DIPEA (67 mg, 0.52 mmol) were added followed by the addition of crude 71 (150 mg, 0.46 mmol) in anhydrous NMP (3 mL). After 2.5 h, the reaction mixture was diluted with diethyl ether and washed successively with water, aqueous NaHCO3, water, and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by flash silica gel chromatography (1:1 hexanes/EtOAc) to afford 210 mg (86%) of 72 as a white-colored foam. Mass spectrum, m/z [523] (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08399683B2
Source dataset	uspto-grants-2013_03
ORD ID	ord-f579f401acc3474da5ce7c7210ae8d7c
Source note	uspto-grants-2013_03