تفاعل #1571600

معادلة التفاعل

(4R,5R)-4-Fluoromethyl-5-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Sodium thiomethoxide

L-proline sodium salt

→

title compound

المردود 86.8%

(4R,5R)-4-Fluoromethyl-2,2-dimethyl-5-(4-methylsulfanyl-phenyl)-oxazolidine-3-carboxylic acid tert-butyl ester

المردود 86.8%

المذيبات

DMSO

ظروف التفاعل

المعالجة

1. 1
   أخرىReaction mixture
2. 2
   أخرىis quenched with water
3. 3
   استخلاصextracted with ethyl acetate
4. 4
   غسيلOrganic layer is washed with brine
5. 5
   تجفيفdried over sodium sulphate
6. 6
   تركيزconcentrated
7. 7
   أخرىpurified by CombiFlash

الإجراء التجريبي

To a solution of (4R,5R)-4-Fluoromethyl-5-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (2.4 g, 5.51 mmol) in DMSO (40 mL) is added Sodium thiomethoxide (0.463 g, 6.621 mmol), CuI (0.105 g, 0.552 mmol) and L-proline sodium salt (0.151 g, 1.103 mmol) and heated the mixture at 90° C. for 24 h. Reaction mixture is quenched with water and extracted with ethyl acetate. Organic layer is washed with brine and dried over sodium sulphate, concentrated and purified by CombiFlash using 120 g column with 9.26% ethyl acetate in hexane as an eluent to afford title compound (1.7 g) as faint yellow solid. 1H-NMR (400 MHz, DMSO): δ 1.42 (s, 9H), 1.47 (s, 3H), 1.59 (s, 3H), 2.47 (s, 3H), 3.73-3.79 (m, 1H), 4.37-4.92 (m, 1H), 4.71-4.94 (m, 1H), 5.01 (d, J=7.44 Hz, 1H), 7.27 (d, J=8.28 Hz, 2H), 7.39 (d, J=8.36 Hz, 2H). LC-MS (m/z): M+H=356.2.

المصدر