Triethylamine → HCID 70001132, compound

To a slurry of glycine ethyl ester hydrochloride (3.5 g, 25 mmol) in dichloromethane (30 ml) was added triethylamine (3.44 ml, 25 mmol) and N-methylisatoic acid anhydride (3.5 g, 20 mmol). After stirring overnight the reaction mixture was washed with water and the organic layer transferred to a round bottomed flask. To this solution was added water (30 ml) followed by bromoacetyl bromide (2.9 ml, 33 mmol). The resulting emulsion was vigorously stirred and neutralized by addition of a saturated aqueous solution of Na2CO3. The organic layer was separated and dried over Na2SO4. After filtration into a round bottomed flask DBU (4.45 ml, 30 mmol) was added to the filtrate. After stirring for 1 h at room temperature the reaction mixture was washed once with aqueous KHSO4 (0.1 N) and twice with aqueous HCl (1N). The aqueous extracts were washed with dichloromethane. The combined organic extracts were dried over Na2SO4, filtered and the solvents evaporated to give (1-methyl-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-acetic acid ethyl ester as a brown oil (5.1 g): MS (EI): 276 (M)+.

1. washwas washed with water
2. customthe organic layer transferred to a round bottomed flask
3. additionTo this solution was added water (30 ml)
4. stirringThe resulting emulsion was vigorously stirred
5. customThe organic layer was separated
6. dry with materialdried over Na2SO4
7. additionwas added to the filtrate
8. stirringAfter stirring for 1 h at room temperature the reaction mixture
9. washwas washed once with aqueous KHSO4 (0.1 N) and twice with aqueous HCl (1N)
10. washThe aqueous extracts were washed with dichloromethane
11. dry with materialThe combined organic extracts were dried over Na2SO4
12. filtrationfiltered
13. customthe solvents evaporated

ORD record

ord-ebe2ef71b8064e4db0148678e43b2cc5

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06506744B1