Potassium Carbonate → (Z)-N-(1-(4-bromophenyl)-1-iodoprop-1-en-3-yl)sarcosine

A solution of (Z)-1-(4-bromophenyl)-1-iodopropene-3-ol C (8.81 g, 26.0 mmol) in CH2Cl2 (220 mL) was chilled in a dry-ice/acetonitrile bath under argon. PPh3 (10.9 g, 41.6 mmol), and N-bromosuccinimide (NBS, 7.40 g, 41.6 mmol) were added. After 1 hour the reaction was quenched with saturated NaHCO3. The mixture was washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated. The residue was immediately taken up into anhydrous acetonitrile (MeCN, 104 mL). t-butyl sarcosine hydrochloride (5.20 g, 28.6 mmol), K2CO3 (35.9 g, 260 mmol), and KI (21.6 g, 130 mmol) were added. The mixture was stirred overnight, then filtered and the filter cake washed with EtOAc. The filtrate was partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4), filtered, and concentrated. Column chromatography (20% EtOAc/hexanes) provided (Z)-N-(1-(4-bromophenyl)-1-iodoprop-1-en-3-yl)sarcosine, tbutyl ester D (9.63 g, 80% over 2 steps) as a light brown oil. 1H NMR (300 MHz, CDCl3) 1.48 (s, 9H), 2.46 (s, 3H), 3.23 (s, 2H), 3.43 (d, 2H), 6.12 (t, 1H), 7.34 (d, 2H), 7.43 (d, 2H).

1. customAfter 1 hour the reaction was quenched with saturated NaHCO3
2. washThe mixture was washed with saturated NaHCO3 and brine
3. dry with materialdried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated
6. filtrationfiltered
7. washthe filter cake washed with EtOAc
8. customThe filtrate was partitioned between EtOAc and water
9. washThe organic phase was washed with brine
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-ab713388fc7f470e94ca5a9ca82d9e73

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06667336B2