Bromoacetic Acid → 2-Benzyloxycarbonylamino-3-(bromoactyl-prop-2-ynyl-amino)-propionic acid methyl ester

DCC (2.27 g, 11.0 mmol) and bromoacetic acid (1.48 g, 10.7 mmol) is added to a solution of 2-benzyloxycarbonylamino-3-(prop-2-ynylamino)-propionic acid methyl ester (3.10 g, 10.7 mmol) in CH2Cl2 at RT. The mixture is stirred overnight then diluted with ether. The white solid which precipitates out is filtered and the filtrate is concentrated to give a yellow oil. The crude product is purified by chromatography eluting with a gradient of 40% EtOAc/hexanes to 50% EtOAc/hexanes to yield the title product (2.1 g, 5.12 mmol) as an oil. 1H NMR (CDCl3, 300 MHz) δ7.30 (m, 5H), 5.70 (d, 1H), 5.10 (s, 2H), 4.63 (m, 1H), 4.15 (d, 2H), 4.00 (m, 1H), 3.80 (s, 3H), 3.75 (s, 2H), 3.70 (dd, 1H), 2.27 (bs, 1H). Ion spray MS, [M+H]+=411, 413, Br pattern.

1. customThe white solid which precipitates out
2. filtrationis filtered
3. concentrationthe filtrate is concentrated
4. customto give a yellow oil
5. customThe crude product is purified by chromatography
6. washeluting with a gradient of 40% EtOAc/hexanes to 50% EtOAc/hexanes

ORD record

ord-356294f83e544092bde454bc39068ad5

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612075B2