1-Hydroxybenzotriazole → tert-butyl N-[(3S)-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]carbamate

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	(2S)-3-[(2-aminophenyl)amino]-2-{[(tert-butoxy)carbonyl]amino}propanoic acid	HCID 22881946	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	tert-butyl N-[(3S)-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]carbamate	HCID 22881971	77.2%

Reaction Steps

To an ice cold solution of (S)-3-(2-amino-phenylamino)-2-tert-butoxycarbonylamino-propionic acid (4 g, 13.54 mmol) in DMF (40 mL) was added EDCI.HCl (2.86 g, 14.89 mmol), HOBT (2.01 g, 14.89 mmol) and DIPEA (7.19 mL, 40.63 mmol). The resulting mixture was stirred for 16 h at RT. The mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was concentrated and the resulting material was purified by silica gel chromatography using to afford the title compound (2.9 g, 77%) as an off white solid. LC-MS: 278 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09409888B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-384fd5ddeac6484a91ff6f5fbb571b23
Source note	uspto-grants-2016_08