Hydrochloric Acid → 3',4'-Diamino-biphenyl-2-sulfonic acid tert-butylamide

HRID 1433178ノート

反応式

HRID 1433178 の反応式
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20]([NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:22])=[O:21])[CH:11]=[CH:10][C:9]=1[NH:28]C(OC(C)(C)C)=O)(C)(C)C.Cl>O1CCOCC1>[C:24]([NH:23][S:20]([C:15]1[C:14]([C:12]2[CH:11]=[CH:10][C:9]([NH2:28])=[C:8]([NH2:7])[CH:13]=2)=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:22])=[O:21])([CH3:27])([CH3:25])[CH3:26]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 579350332-Tert-butoxycarbonylamino-5-(2-tert-butylaminosulfonyl-phenyl)-phenyl carbamic acid tert-butyl ester

生成物 1

HCID 579349643',4'-Diamino-biphenyl-2-sulfonic acid tert-butylamide収率 185.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

2-tert-butoxycarbonylamino-5-(2-tert-butylaminosulfonyl-phenyl)-phenyl carbamic acid tert-butyl ester (5.4 g, 10.3 mmol) in a solution of 4M HCl in 1,4-dioxane (250 mL) was stirred at room temperature for 4 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane, and the solution was washed with saturated sodium bicarbonate and water (pH=7). The organic layer was dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by chromatography (silica, EtOAc: hexanes, 1:1) to afford the title compound as a brown viscous oil (6.1 g, 92% yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 8.12 (dd, 1H, J=7.9, J=1.7), 7.51 (td, 1H, J=7.5 Hz, J=1.5 Hz), 7.42 (td, 1H, J=7.6 Hz, J=1.3 Hz), 7.30 (dd, 1H, J=7.8, J=1.5), 6.94 (d, 1H, J=1.9), 6.80 (m, 2H), 3.80 (s, NH), 3.50 (br s, 4H), 0.98 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C16H21N3O2S: 320.42 (M+H), Found 320.9.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washthe solution was washed with saturated sodium bicarbonate and water (pH=7)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by chromatography (silica, EtOAc: hexanes, 1:1)

出典と根拠

ORDレコード
ord-8049551be6f94b9fa3295315f4df774b
出典データセット
uspto-grants-2009_11
特許番号
US07612211B2

反応ノート

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