Triethylamine → HCID 14084268, compound

About 6.02 g of ethyl glycinate hydrochloride, 14.39 g of triethylamine, and 10 ml of toluene were mixed in a round-bottom reaction flask cooled with an ice bath. To this mixture was added, in a dropwise fashion, a solution of 21.1 g of trimethylsilyl trifluoromethanesulfonate in 50 ml of toluene. The resulting mixture was stirred at room temperature for 19 hours to give a biphasic mixture. The top layer was transferred to another flask, and the bottom layer was extracted with 40 ml of toluene. The combined toluene solution was evaporated under vacuum. The residue was extracted with 100 ml of hexane, and the hexane layer was evaporated under vacuum, yielding ethyl [bis(trimethylsilyl)amino]acetate, also known as ethyl N,N-bis(trimethylsilyl)glycinate (BTMSEG), as a colorless liquid (9.23 g, 87% yield). The 1H NMR data (C6D6, 25° C., referenced to tetramethylsilane) of the product are listed as follows: δ 3.89 (quartet, 2 H, OCH2 protons), 3.51 (singlet, 2 H, NCH2 protons), 0.90 (triplet, 3 H, CH3 protons), 0.14 (singlet, 18H, Si—CH3 protons). From the 1H NMR data, the structure of the product was determined to be as follows:

1. temperaturecooled with an ice bath
2. additionTo this mixture was added, in a dropwise fashion
3. customto give a biphasic mixture
4. customThe top layer was transferred to another flask
5. extractionthe bottom layer was extracted with 40 ml of toluene
6. customThe combined toluene solution was evaporated under vacuum
7. extractionThe residue was extracted with 100 ml of hexane
8. customthe hexane layer was evaporated under vacuum

ORD record

ord-fb8369684f324f03a2fa47997f895da9

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895670B2