Oxalyl chloride → HCID 54202635, compound

Participants

Reaction Conditions

Reaction Steps

(2R,3R)-3-(3,4-Dimethoxyphenylsulfanyl)-2-methyl-7-phenylheptanoic acid (0.33 g, 0.85 mmol) is dissolved in CH2Cl2 (4 mL) and cooled to 0° C. and to this is added 2 M oxalyl chloride in CH2Cl2 (1.3 mL, 2.6 mmol) over 3 minutes. After 10 minutes the ice bath is removed and the reaction is stirred at room temperature for 2 hours. The reaction is concentrated in vacuo and azeotroped with chloroform twice. The residue is dissolved in CH2Cl2 (4 mL), cooled in ice and O-trimethylsilylhydroxylamine (0.32 mL, 2.6 mmol) is added over 2 minutes. After 10 minutes the reaction is concentrated in vacuo. The residue is dissolved in CH2Cl2 (50 mL) and washed with 1 N HCl (20 mL). The organic layer is dried over MgSO4 and the solvent removed in vacuo to give (+)-(2R,3R)-3-(3,4-Dimethoxyphenylsulfanyl)-2-methyl-7-phenylheptanoic acid hydroxyamide (0.27 g, 79%): [a]D23 +40° (c=1.0, CHCl3); 1H NMR (300 MHz, CD3OD) δ 7.25-7.20 (m, 2H), 7.13-7.11 (m, 3H), 7.00-6.96 (m, 2H), 6.88 (d, J=8.0 Hz, 1H), 3.81 (s, 3H), 3.78 (s, 3H), 3.01-2.95 (m, 1H), 2.57-2.55 (m,1H), 2.23-2.15 (m, 1H), 1.71-1.41 (m, 6H), 1.34 (d, J=6.9 Hz, 3H); MS (FAB) m/e 404 (M+H)+.

Provenance & Evidence