background and overview[1]
di-tert-butyl azidooxalic acid can be used as a pharmaceutical synthesis intermediate. if di-tert-butylazidooxalic acid is inhaled, please move the patient to fresh air; if there is skin contact, take off contaminated clothing, rinse the skin thoroughly with soap and water, and seek medical treatment if you feel uncomfortable; if there is eye contact , you should separate your eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse your mouth immediately, do not induce vomiting, and seek medical attention immediately.
preparation[1]
di-tert-butyl azidooxalic acid is prepared as follows:
the specific steps are as follows: under ice bath conditions, drop a 50ml solution of hydrazine monohydrate (5.85g, 85%, 200mmol) into a 50ml methanol solution of boc anhydride (48g, 220mmol) within 30 minutes, and the resulting mixed solution stir at room temperature for 3 hours, spin the methanol to dryness, and add 250 ml of n-hexane. the resulting white solid is suction-filtered and washed with n-hexane to obtain 19.34 g of white solid di-tert-butyl azide oxalic acid with a yield of 84%. 1h nmr (300mhz, cdcl3): δ = 6.60 (s, 2h), 1.47 (s, 9h); 13c nmr (50mhz, cdcl3) δ = 156.0, 84.1, 28.3.
apply[1]
di-tert-butyl azidooxalic acid can be used as a pharmaceutical synthesis intermediate. if the following reaction occurs:
the specific steps are as follows: di-tert-butyl azidooxalic acid (11.6g, 50mmol), 50ml sodium hydroxide aqueous solution (30%wt), 1,2-dichloroethane (100ml), catalytic amount of tetrabutyl ammonium bromide (0.5g) was mixed. the mixture was heated at 55°c for 10 hours, cooled, and the organic phase was separated. the aqueous phase was extracted with dichloromethane. the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was spin-dried. column chromatography (petroleum) ether: ethyl acetate = 10:1) to obtain a colorless viscous liquid (13.8 g, yield 75%). 1h nmr (300mhz, cdcl3): δ=3.53–3.97(m,8h),1.49(m,18h).
main reference materials
[1] cn201410570945.7 a complex containing hydrazine-type nitrogen and phosphorus ligands and its application in the catalytic hydrogenation of esters. application date 20141023, wuhan kaitris technology co., ltd.