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

HRID 1433178Notes

Reaction equation

HRID 1433178 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-8049551be6f94b9fa3295315f4df774b
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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