4-Methylmorpholine → 2,2-Dimethyl-propanoic Acid [3-Chloro-2-[[[2-[(triphenylmethyl)amino]-5-thiazolyl]carbonyl]amino]phenyl]methyl Ester

Participants

Reaction Steps

To a solution of compound 7a (7.36 g, 14 mmol) in THF (200 mL) at 5° C. were added N-methylmorpholine (3.1 mL, 28 mmol) followed by slow addition of trimethylacetyl chloride (8a, 1.8 mL, 21 mmol). The reaction mixture was allowed to warm to room temperature over a period of 3 h. A solution of saturated NH4Cl in H2O (500 mL) was added. The mixture was extracted with EtOAc (2×250 mL). The combined extracts were washed with 1N HCl (500 mL), saturated NaHCO3 (500 mL), dried over MgSO4. The solution was filtered and concentrated in vacuo to give compound 9a as a white solid (8.90 g, 100% yield). 1H NMR (500 MHz, CDCl3) δ 1.16 (s, 9H), 5.01 (s, 2H), 7.20-7.40 (m, 18H), 7.79 (s, 1H), 8.30 (bs, 1H).

Provenance & Evidence