Methyl iodide → HCID 58913376, compound

Temperature

-78 °C

A solution of 5.0 g (15 mmol) of Ethyl 2-(2-tert-butoxycarbonylaminothiazol-yl)-4-pentenoate (Intermediate 34) in 100 mL of THF at −78° C. was treated with 25 mL (43 mmol) of 1.7 M t-butyl lithium in hexane for 30 min. To the resulting red solution was added a neat solution of 2.82 g (20 mmol) of iodomethane. The reaction was stirred at −78° C. for 2 h and then warmed to 0° C. and stirred for 0.5 h. The reaction was quenched with 10 g of citric acid in 100 mL of water. The mixture was stirred overnight, evaporated to remove THF and extracted with CH2Cl2 (2×100 mL). The combined organic phases were washed with brine and dried over Na2SO4 and concentrtaed in vacuo. MPLC using 1:9 v/v EtOAc/hexanes as the eluant afforded 0.8 g of the title compound as an oil. 1H NMR (300 MHz, CDCl3): δ 1.15–1.22 (m, 3H), 1.42–1.67 (d, 12H), 2.67–2.76 (m, 2H), 4.09–4.17 (m, 2H), 5.00–5.10 (m, 2H), 5.50–5.65 (m, 1H), 6.63 (1, 1H), 7.91 (wide, 1H).

1. temperaturewarmed to 0° C.
2. stirringstirred for 0.5 h
3. customThe reaction was quenched with 10 g of citric acid in 100 mL of water
4. stirringThe mixture was stirred overnight
5. customevaporated
6. customto remove THF
7. extractionextracted with CH2Cl2 (2×100 mL)
8. washThe combined organic phases were washed with brine
9. dry with materialdried over Na2SO4

ORD record

ord-7f4eb688b3644fdfa989c78f24065da0

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07247725B2