3-Amino-1-propanol → HCID 131731275, compound

Participants

Role	Name	HCID	Charge
Reactant	3-Amino-1-propanol	HCID 9086	—
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	Auristatin F	HCID 67472795	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 131731275	HCID 131731275	68%

Reaction Conditions

Temperature	23 °C

Reaction Steps

Auristatin F (150 mg, 0.201 mmol), HATU (153.0 mg, 0.402 mmol), and diisopropylethylamine (108 μL, 0.603 mmol) were taken up in DMF (5 mL) and 3-aminopropan-1-ol (45.9 μL, 0.603 mmol) was added. The mixture was stirred at 23° C. for 45 minutes at which time LCMS analysis showed complete disappearance of the starting material. Reduction of the volume to 1.4 mL under high vacuum followed by purification via preparative HPLC (10-90 solvent B gradient over 20 minutes eluting with 0.1% TFA/Water, 0.1% TFA/CH3CN) afforded the title compound as white solid (109 mg, 68% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08821850B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-e1e02cc4069141228fd25e1f04d271b5
Source note	uspto-grants-2014_09