1,5-Naphthalenedisulfonic acid → (+/-)-Methyl alpha-fluoromethylhistidinate 1,5-naphthalene disulfonate

반응식

Cl.[F:2][CH2:3][C@@:4]([C:12]([OH:14])=[O:13])([CH2:6][C:7]1[N:11]=[CH:10][NH:9][CH:8]=1)[NH2:5].[CH:15]([O-])([O-])OC.[C:20]1([S:34]([OH:37])(=[O:36])=[O:35])[C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([S:30]([OH:33])(=[O:32])=[O:31])[C:24]=2[CH:23]=[CH:22][CH:21]=1>CO>[C:20]1([S:34]([OH:37])(=[O:36])=[O:35])[C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([S:30]([OH:33])(=[O:32])=[O:31])[C:24]=2[CH:23]=[CH:22][CH:21]=1.[F:2][CH2:3][C@@:4]([C:12]([O:14][CH3:15])=[O:13])([CH2:6][C:7]1[N:11]=[CH:10][NH:9][CH:8]=1)[NH2:5]

참가 물질

실험 절차

Into a Fisher-Porter tube there was charged 5 g of (±) α-fluoromethylhistidine hydrochloride, 100 ml of methanol, 45 ml of methyl orthoformate and 9.7 g of naphthalene-1,5-disulfonic acid. The tube was sealed and heated in a steam bath overnight. The tube was cooled in an ice bath and the crystalline product (naphthalene-1,5 disulfonic acid salt of α-fluoromethylhistidine) was filtered and returned to the Fisher-Porter tube. Methanol (120 ml), methyl orthoformate (55 ml), and naphthalene-1,5 disulfonic acid (9.4 g) were added, the tube sealed and heated overnight in a steam bath, then cooled in an ice bath for ca. 5 hours. The crystals of (±)-methyl α-fluoromethylhistidinate 1,5-naphthalene disulfonate formed were filtered, washed with cold methanol and diethyl ether and dried in vacuo.