OSCAR-CM Isopropyl OSCAR-CM 3-(hydroxymethyl)pyridine-2-carboxylate COMMA , -LRB- ( CD 200 NN-MASS g COMMA , CD 1.02 NN-AMOUNT mol STOP ; VB-SYNTHESIZE prepared IN-AS as IN-IN in OSCAR-CM -P STOP . NNP Ornstein FW et. FW al. NNP J STOP . NNP Med STOP . NNP Chem STOP . CD 1989 COMMA , CD 32 COMMA , CD 827 -RRB- ) COMMA , OSCAR-CM methyl OSCAR-CM N-[(4-methylphenyl)sulfonyl]glycinate -LRB- ( CD 249 NN-MASS g COMMA , CD 1.02 NN-AMOUNT mol -RRB- ) COMMA , CC and OSCAR-CM triphenylphosphine -LRB- ( CD 403 NN-MASS g COMMA , CD 1.5 NN-AMOUNT mol -RRB- ) VBD were VB-DISSOLVE dissolved IN-IN in JJ-CHEM dry OSCAR-CM THF -LRB- ( CD 3000 NNS mls -RRB- ) CC and VB-COOL cooled TO to CD zero NN-TEMP degrees IN-UNDER under OSCAR-CM N2 STOP . DT-THE The OSCAR-CM diethylazodicarboxylate -LRB- ( OSCAR-CM DEAD -RRB- ) -LRB- ( CD 267.6 NN-MASS g COMMA , CD 1.5 NN-AMOUNT mol -RRB- ) VBD was VB-DISSOLVE dissolved IN-IN in JJ-CHEM dry OSCAR-CM THF -LRB- ( CD 250 NNS mls -RRB- ) CC and VB-SUSPEND placed IN-IN in DT a CD 500 NN-VOL ml NN-ADD addition NN-APPARATUS funnel STOP . DT-THE The OSCAR-CM DEAD VBD was VB-ADD added RB dropwise IN-OVER over CD 1 NN-TIME hour STOP . DT-THE The NN-CHEMENTITY ice NN-APPARATUS bath VBD was VB-REMOVE removed CC and DT-THE the NN-CHEMENTITY reaction VBD was VBN allowed TO to VB-HEAT warm RB slowly TO to NN-TEMP RT STOP . IN-AFTER After CD 2 NN-TIME hours COMMA , DT-THE the NN-CHEMENTITY reaction VBD was VBN checked IN-BY by NNP HPLC CC and DT some OSCAR-CM glycinate VBD remained STOP . RBR More VBG starting NN-CHEMENTITY reagents VBD were VB-ADD added CC and DT-THE the NN-CHEMENTITY reaction VBD was VB-WAIT left TO to VB-STIR stir IN at NN-TEMP RT STOP . IN-AFTER After CD 30 NN-TIME min COMMA , DT-THE the NN-CHEMENTITY reaction VBD was VBN checked RB again CC and VBD saw DT a RB very JJ small NN amount IN-OF of DT-THE the OSCAR-CM glycinate JJ-CHEM remaining STOP . VB-CONCENTRATE Concentrated NN-SYNTHESIZE reaction IN down TO to DT a JJ-CHEM reddish-orange NN-STATE oil WDT that VBD was VBN carried IN onto DT-THE the JJ next NN-METHOD step STOP . NN-ADD Addition IN-OF of CD 10 NN-VOL mL OSCAR-CM methanol STOP .