Diisopropylethylamine → 2-Chlorobenzene-1-sulfonic acid

HRID 482092노트

반응식

HRID 482092 반응식
N1CCCC(COC2C=C([O:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])(=[O:19])=[O:18])C=C(C)C=2)C1.C(N(CC)C(C)C)(C)C.NN=CS(O)(=O)=O>CN(C=O)C>[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[S:17]([OH:19])(=[O:18])=[O:16]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 3013981Aminoiminomethane-sulphonic acidHCID 536550322-Chlorobenzenesulfonic acid 3-[(piperidin-3-yl)methoxy]-5-methylphenyl ester

생성물 1

HCID 135314532-Chlorobenzene-1-sulfonic acid수율 82.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 2-chlorobenzenesulfonic acid 3-[(piperidin-3-yl)methoxy]-5-methylphenyl ester (396 mg, 1.0 mmol), as prepared in the preceding step, in DMF (10 mL) containing N,N-diisopropylethylamine (0.5 mL) and aminoiminomethanesulfonic acid (248 mg, 2.0 mmol) was stirred at room temperature overnight. The DMF was removed in vacuo and the residue was purified by flash column chromatography (90:10 methylene chloride:methanol saturated with NH3) to give the title compound as a white foam (159 mg, 36%). 1H-NMR (300 MHz, CDCl3) δ 1.45-1.92 (m, 4H), 2.11 (m, 1H), 2.23 (s, 3H), 3.07 (m, 2H), 3.81 (d, 2H), 3.92 (m, 2H), 6.50 (s, 2H), 6.61 (s, 1H), 7.24 (bs, 3H), 7.40 (m, 1H), 7.63 (m, 2H), 7.95 (dd, 1H). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C20H24N3 O4SCl: 438.1 (M+H), 460.1 (M+Na), Found: 438.5, 460.5.

후처리

  1. customThe DMF was removed in vacuo
  2. customthe residue was purified by flash column chromatography (90:10 methylene chloride:methanol saturated with NH3)

출처 및 근거

ORD 기록
ord-c3554de2a0044adfa27dfbcc7fab88a2
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05792769

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