(4-Tert-butoxycarbonylamino-2'-trifluoromethanesulfonyl-biphenyl-3-yl)-carbamic acid tert-butyl ester → 2'-Trifluoromethanesulfonyl-biphenyl-3,4-diamine

HRID 1433223Notes

Reaction equation

HRID 1433223 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([C:31]([F:34])([F:33])[F:32])(=[O:30])=[O:29])[CH:11]=[CH:12][C:13]=1[NH:14]C(OC(C)(C)C)=O)(C)(C)C>Cl.O1CCOCC1>[F:33][C:31]([F:32])([F:34])[S:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:10]1[CH:11]=[CH:12][C:13]([NH2:14])=[C:8]([NH2:7])[CH:9]=1)(=[O:29])=[O:30]

Participants

4

Reactant 1

HCID 57934932(4-Tert-butoxycarbonylamino-2'-trifluoromethanesulfonyl-biphenyl-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 579349912'-Trifluoromethanesulfonyl-biphenyl-3,4-diamineYield 98%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (4-tert-butoxycarbonylamino-2′-trifluoromethanesulfonyl-biphenyl-3-yl)-carbamic acid tert-butyl ester (0.072 g, 0.228 mmol) in 4M HCl in dioxane (3 mL) was stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc, 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 to provide the title compound as a yellow oil (0.043 g, 98%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  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

Sources & evidence

ORD record
ord-0a35c79812274bb3be3d5378182e3d7a
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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