Reacción #81862

Ecuación de reacción

8j

3-Chloro-7-[[[2-(3-hydroxy-2-pyridinyl)-4-thiazolyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Diphenylmethyl Ester

Et3SiH

trifluoroacetic acid

9a

3-[(Acetyloxy)methyl]-7-[[[2-(2-hydroxyphenyl)-4-thiazolyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

→

9j

Rendimiento 90.2%

3-Chloro-7-[[[2-(3-hydroxy-2-pyridinyl)-4-thiazolyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

Rendimiento 90.2%

Disolventes

ClCH2CH2Cl

Condiciones de reacción

Procedimiento

The procedure used for the preparation of 9a was repeated with 8j (186 mg, 0.301 mmol), Et3SiH (0.480 mL, 3.01 mmol), and trifluoroacetic acid (0.927 mL, 12.0 mmol) in dry ClCH2CH2Cl (6 mL) at 0° C. under nitrogen to give 9j (123 mg, 90%) a s a brownish solid after crystallization from THF/CH2Cl2 /hexane. mp 175° C. (dec); IR (KBr) 3600-2700 (br), 3277, 1780, 1730, 1663 cm-1 ; 1H NMR (DMSO-d6) δ3.63 (1H, d, J=18.0 Hz), 3.78 (2H, s, CH2), 3.98 (1H, d, J=18.0 Hz), 5.15 (1H, d, J=4.8 Hz), 5.69 (1H, dd, J=8.1 and 4.8 Hz), 7.37 (1H, dd, J=8.4 and 4.3 Hz), 7.44 (1H, dd, J=8.4 and 1.1 Hz), 7.58 (1H, s), 8.14 (1H, dd, J=4.3 and 1.1 Hz), 9.23 (1H, d, J=8.1 Hz, NH), 11.62 (1H, s, OH), 13.80 (1H, br s, CO2H); FDMS m/z 453 (M+ +1, 35Cl), 455 (M+ +1, 37Cl); HRMS m/z Calcd for C17H1435ClN4O5S2 (M+ +1): 453.0094, Found: 453.0090.

Fuente