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

HRID 1433191Notes

Reaction equation

HRID 1433191 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:10][C:9]=1[NH:24]C(OC(C)(C)C)=O)(C)(C)C>Cl.O1CCOCC1>[CH3:23][S:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:11]1[CH:12]=[CH:13][C:8]([NH2:7])=[C:9]([NH2:24])[CH:10]=1)(=[O:21])=[O:22]

Participants

4

Reactant 1

HCID 57935002(3-Tert-butoxycarbonylamino-2'-methanesulfonyl-biphenyl-4-yl)-carbamic acid tert-butyl ester

Product 1

HCID 579349992'-Methanesulfonyl-biphenyl-3,4-diamineYield 98%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (3-tert-butoxycarbonylamino-2′-methanesulfonyl-biphenyl-4-yl)-carbamic acid tert-butyl ester (12.47 g, 0.0270 mol) in 4M HCl in dioxane (120 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 (6.93 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-dc5cbba8bdd44e4e89291de0af726561
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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