Triethylamine → HCID 73834442、化合物

A solution of ethyl (4-methyl-1,3-thiazol-2-yl)acetate (ENAMINE, 300 mg, 1.619 mmol) in acetonitrile (ACN) (12 mL) was treated with triethylamine (FLUKA, 0.339 mL, 2.429 mmol) at 0° C. After 20 minutes 4-acetamidobenzenesulfonyl azide (ALDRICH, 389 mg, 1.619 mmol) was added and the mixture was allowed to reach room temperature overnight. Then, 4-acetamidobenzenesulfonyl azide (ALDRICH, 94 mg, 0.391 mmol) was added and continued stirring at room temperature for 2 h. Reaction mixture was concentrated and residue was triturated with a mixture 1:1 Et2O-hexane and filtered. Solid was washed several times with the same mixture. The filtrate was concentrated to give 310 mg of crude. It was purified on a 10 g silica cartridge and eluted manually with linear gradient 0-50% hexane-ethyl acetate to yield the title compound (200 mg, 0.947 mmol, 58.5% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm: 7.49 (d, 1H), 4.34 (q, 2H), 2.60 (s, 3H), 1.32 (t, 3H). [ES+MS] m/z 212 (MH+).

1. customReaction mixture
2. concentrationwas concentrated
3. customresidue was triturated with a mixture 1:1 Et2O-hexane
4. filtrationfiltered
5. washSolid was washed several times with the same mixture
6. concentrationThe filtrate was concentrated
7. customto give 310 mg of crude
8. customIt was purified on a 10 g silica cartridge
9. washeluted manually with linear gradient 0-50% hexane-ethyl acetate

ORDレコード

ord-a43e85348bdf4a3c8dbb968694c1a896

出典データセット

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08524750B2