Hydrochloric Acid → 2-(3',4'-Diamino-biphenyl-2-sulfonyl)-ethanol

HRID 1433227Notes

Reaction equation

HRID 1433227 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]([CH2:31][CH2:32][OH:33])(=[O:30])=[O:29])[CH:11]=[CH:12][C:13]=1[NH:14]C(OC(C)(C)C)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:7][C:8]1[CH:9]=[C:10]([C:22]2[C:23]([S:28]([CH2:31][CH2:32][OH:33])(=[O:30])=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:11]=[CH:12][C:13]=1[NH2:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57934947[4-Tert-butoxycarbonylamino-2'-(2-hydroxy-ethanesulfonyl)-biphenyl-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 579349382-(3',4'-Diamino-biphenyl-2-sulfonyl)-ethanolYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[4-tert-butoxycarbonylamino-2′-(2-hydroxy-ethanesulfonyl)-biphenyl-3-yl]-carbamic acid tert-butyl ester (0.233 g, 0.476 mmol) in a solution of 4M HCl in dioxane (6 mL) was stirred at room temperature for 2 hours. 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 (0.136 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-75426d1fe961426f8c1a669d324f3dc6
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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