Dichloromethane → glycyl-D-alanine benzyl ester hydrochloride

To a cold (0° C.) solution of 100 ml. methylene chloride containing 10 g. (57 mmol) of N-t-butyloxycarbonylglycine, 20 g. (57 mmol) of D-alanine benzyl ester p-toluene sulfonic acid salt and 5.77 g. (57 mmol) of triethylamine was added 12.3 g. (60 mmol) of dicyclohexylcarbodiimide and the resulting reaction mixture allowed to warm to room temperature. After 18 hours the mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in 200 ml. of ethyl acetate and the organic layer washed with 2.5% hydrochloric acid, water, a saturated sodium bicarbonate solution and a brine solution. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure. To the resulting oil 200 ml. of dioxane saturated with hydrogen chloride was added. After 30 minutes 400 ml. of diethyl ether was added and the product filtered under nitrogen, 10.9 g. (70% yield).

1. customTo a cold (0° C.) solution of 100 ml
2. filtrationAfter 18 hours the mixture was filtered
3. concentrationthe filtrate concentrated in vacuo
4. dissolutionThe residue was dissolved in 200 ml
5. washof ethyl acetate and the organic layer washed with 2.5% hydrochloric acid, water
6. customThe organic layer was separated
7. dry with materialdried over magnesium sulfate
8. customevaporated under reduced pressure
9. additionof dioxane saturated with hydrogen chloride was added
10. additionof diethyl ether was added
11. filtrationthe product filtered under nitrogen

ORD record

ord-042fbd86b6fe436b88f44678e39f7b6d

Source dataset

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05245079