1-Hydroxybenzotriazole → N-(Morpholinocarbonyl)-L-phenylalanine S-methyl-L-cysteine methyl ester

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	CP 84364	HCID 664657	—
Reactant	Methyl (2R)-2-amino-3-(methylsulfanyl)propanoate	HCID 1277655	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Triethylamine	HCID 8471	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	N-(Morpholinocarbonyl)-L-phenylalanine S-methyl-L-cysteine methyl ester	HCID 67865905	78%

Reaction Steps

To a solution of 0.96 g N-(morpholinocarbonyl)-L-phenylalanine 3 and 0.55 g S-methyl-L-cysteine methyl ester in 50 mL anhydrous methylene chloride at ambient temperature was added 0.50 mL triethylamine, 0.51 g 1-hydroxybenzotriazole and 0.70 g 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride. After being stirred for 4 h, the solution was diluted with 100 mL ethyl acetate and was washed with 2×35 mL 0.1N hydrochloric acid solution and 2×35 mL 0.1N sodium hydroxide solution. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to afford 1.15 g of the desired solid dipeptide.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05034376
Source dataset	uspto-grants-1991_07
ORD ID	ord-9f93c1358bdf4432a0b26833ddc82d78
Source note	uspto-grants-1991_07