1-Hydroxybenzotriazole → HCID 90221098, compound

https://huagongshe.com/reaction/1481906

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acid	HCID 7009590	—
Reactant	HCID 90220939	HCID 90220939	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 90221098	HCID 90221098	92.54%

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a stirred solution of (S)-3-amino-1-(2-methyl-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5 tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile hydrochloride (305 mg, 0.778 mmol) in DMF (10 mL) was added Boc-N-Me-Ala-OH (173.912 mg, 0.856 mmol), HOBT (115.645 mg, 0.856 mmol) and DIPEA (0.67 mL, 3.89 mmol). After 10 min, the mixture was cooled to 0° C. and HBTU (324.63 mg, 0.856 mmol) was added. After 2 h, the mixture was diluted with ethyl acetate, washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to afford the title compound (390 mg, 92.54%) as an off white solid. LC-MS: 542.0 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09409888B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-76bbca6ba9b940ee83500e5ea5ca0c73
Source note	uspto-grants-2016_08