Diisopropylethylamine → HCID 67514413, compound

https://huagongshe.com/reaction/1965198

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Z-N-Me-Ala-OH	HCID 7016365	—
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 67609205	HCID 67609205	—
Reactant	HCID 131730510	HCID 131730510	—
Solvent	Water	HCID 962	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	HCID 67514413	HCID 67514413	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

A solution containing 56 (5.10 g, 15.6 mmol) and DIPEA (3.6 mL, 20.3 mmol) in NMP (20 mL) was cooled to 0° C. In a separate flask at 0° C., Cbz-N(Me)Ala-OH (4.1 g, 17.2 mmol), HATU (6.6 g, 17.2 mmol), and DIPEA (3.6 mL, 20.3 mmol) were dissolved in NMP (80 mL). A portion of the HATU/Cbz-N(Me)Ala-OH solution (72 mL, ˜1.0 equiv) was then added to the cooled solution of 56. After 45 min, the reaction mixture was diluted with water and extracted with EtOAc. The combined organic extracts were washed successively with 10% H3PO4, water, saturated aqueous NaHCO3, water, and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 7.0 g (82%, 2 steps) of 57 as a white foam. Mass spectrum, m/z [546.0] (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08415486B2
Source dataset	uspto-grants-2013_04
ORD ID	ord-69598a1f841742e287e443a01a755112
Source note	uspto-grants-2013_04