Hydrochloric Acid → Glycine, N-2-propen-1-yl-, ethyl ester, hydrochloride (1:1)

To a solution of N-allylglycine ethyl ester (10.0 g, 70.0 mmol, 1 equiv) in Et2O (260 mL) and hexane (1.3 L) at 23° C. was slowly added 4.0 M HCl in dioxane (16.6 mL, 66.5 mmol, 0.95 equiv) over the course of 35 min via addition funnel. Following the addition the suspension was stirred a further 40 min, then the product was isolated via filtration through a glass frit, washing with hexane (200 mL). The collected white solid was transferred to a flask and placed under vacuum (0.5 mm Hg) for 1 h to give 11.5 g of the desired product as a white solid. The reaction was repeated on the same scale to yield a total of 22.73 g (127 mmol, 90%) of the desired amine hydrochloride 21f (R9b=H, m=1) as a white solid: 1H NMR (300 MHz, DMSO-d6) 9.50 (s, 2H), 5.95-5.81 (m, 1H), 5.49-5.37 (m, 2H), 4.21 (q, J=7.2 Hz, 2H), 3.92 (s, 2H), 3.59 (d, J=6.6 Hz, 2H), 1.24 (t, J=7.2 Hz, 3H); MS (ESPOS): 144.1 [M+H]+.

1. customat 23° C.
2. customover the course of 35 min
3. additionvia addition funnel
4. additionthe addition the suspension
5. customthe product was isolated via filtration through a glass frit
6. washwashing with hexane (200 mL)
7. customThe collected white solid was transferred to a flask
8. waitplaced under vacuum (0.5 mm Hg) for 1 h

ORD record

ord-79aa87fdf52d41029154685b8874bc8e

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361743B2