Triethylamine → Methyl 5-(2-(benzyloxycarbonylamino)-4-methylpentanamido)-2-hydroxybenzoate

https://huagongshe.com/en/reaction/85359

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Methyl 5-amino-2-hydroxybenzoate	HCID 135127	—
Reactant	2-(((Benzyloxy)carbonyl)amino)-4-methylpentanoic acid	HCID 246673	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Acetonitrile	HCID 6342	—
Product	Methyl 5-(2-(benzyloxycarbonylamino)-4-methylpentanamido)-2-hydroxybenzoate	HCID 59193171	51.8%

Reaction Steps

A mixture of 2-(benzyloxycarbonylamino)-4-methylpentanoic acid (1.0 g, 3.8 mmol), methyl 5-amino-2-hydroxybenzoate (0.66 g, 3.95 mmol) and Et3N (0.76 g, 7.6 mmol) were dissolved in CH3CN (10 mL) and HATU (1.50 g, 3.95 mmol) was added. The mixture was stirred (RT, 16 h). The solvent was removed under reduced pressure. Brine (50 mL) was added to the resulting residue, and the mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed successively with 2N HCl (3×50 mL), brine (50 mL), 5% NaHCO3 (50 mL×3), brine (50 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography (CH2Cl2) to give methyl 5-(2-(benzyloxycarbonylamino)-4-methylpentanamido)-2-hydroxybenzoate as a white solid (0.81 g, 51.8%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08846972B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-8c0016c9b864480fb9a4363026e92bc2
Source note	uspto-grants-2014_09