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

HRID 1433178노트

반응식

HRID 1433178 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8049551be6f94b9fa3295315f4df774b
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612211B2

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