Triethylamine → HCID 23519196, compound

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine	HCID 2733845	—
Reactant	Ethyl S-benzyl-(R)-cysteinate hydrochloride (1:1)	HCID 12839759	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 23519196	HCID 23519196	—

Reaction Steps

A mixture of S-benzyl-L-cysteine ethyl ester hydrochloride (7.98 g, 29 mmol), BOC-α-methylalanine (5.89 g, 29 mmol), triethylamine (2.93 g, 29 mmol), 1-hydroxybenzotriazole (HOBT, 3.92 g, 29 mmol) and EDCI (5.57 g, 29 mmol) in methylene chloride (200 mL) is stirred under an argon atmosphere at room temperature overnight. The reaction mixture is evaporated to dryness and the residue is dissolved in ethyl acetate (200 mL). The solution is washed with water (50 mL), 1 N HCl (50 mL), water (50 mL), 5% sodium bicarbonate (50 mL), water (50 mL) and finally brine (25 mL). The solution is then dried over sodium sulfate, filtered and evaporated to dryness to give N-[2-(BOC-amino)-2-methylpropionyl]-S -benzyl-L-cysteine ethyl ester.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06777443B2
Source dataset	uspto-grants-2004_08
ORD ID	ord-dc65398f20b84385a389abd1f59336fe
Source note	uspto-grants-2004_08