Hydrochloric Acid → octanedioic acid [4-(3-Nitro-phenyl)-thiazol-2-yl]-amide

HRID 243624

반응식

HRID 243624 반응식
C[O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=2)[N:17]=1)=[O:11].O[Li].O.Cl>CO.O>[N+:24]([C:20]1[CH:19]=[C:18]([C:16]2[N:17]=[C:13]([NH:12][C:10](=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:27])=[O:2])[S:14][CH:15]=2)[CH:23]=[CH:22][CH:21]=1)([O-:26])=[O:25]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 44550802octanedioic acid [4-(3-Nitro-phenyl)-thiazol-2-yl]-amide methyl ester

생성물 1

HCID 16733292octanedioic acid [4-(3-Nitro-phenyl)-thiazol-2-yl]-amide수율 85.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a solution of compound 14 (0.391 g, 1.0 mmol) in a mixture of MeOH (10 ml) and water (10 ml) was added LiOH—H2O (0.839 g, 20.0 mmol), and the mixture was stirred at room temperature for 3 hour. Then the reaction mixture was acidified with 1N HCl dropwise to pH 5 and extracted with EtOAc. The organic layer was washed with water and saturated brine and dried over Na2SO4. The solvent was evaporated to give compound 18 (0.322 g, 85.6%). 1H NMR (300 MHz, DMSO-d6) δ12.3 (1H, s), 8.72 (1H, s), 8.33 (1H, d, J=7.6 Hz), 8.16 (1H, dd, J=7.9, 2.8 Hz), 7.91 (1H, s), 7.72 (1H, t, J=8.0 Hz), 2.45 (2H, t, J=6.5 Hz), 2.19 (2H, t, J=5.7 Hz), 1.60 (2H, brs), 1.49 (2H, t, J=6.3 Hz), 1.30-1.18 (4H, m). 13C NMR (75 MHz, DMSO-d6) M75.3, 172.5, 159.2, 149.1, 147.1, 136.6, 132.5, 131.2, 123.0, 120.9, 111.2, 35.7, 34.4, 31.2, 29.1, 25.3, 25.1.

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-dcd20dc49b1a4bfbb291063c427c12f2
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653278B2

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