Hydrochloride methanol → ethyl 5-[(1R)-1-aminoethyl]-2-[(methylsulfonyl)amino]benzoate

HRID 230591Notes

Reaction equation

HRID 230591 reaction equation
C([S@]([NH:7][C@@H:8]([C:10]1[CH:11]=[CH:12][C:13]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[C:14]([CH:20]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:9])=O)(C)(C)C.Cl.CO>CO>[NH2:7][C@@H:8]([C:10]1[CH:11]=[CH:12][C:13]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[C:14]([CH:20]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:9]

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 57762930Ethyl5-((1R)-1-{[(R)-tert-butylsulfinyl]amino}ethyl)-2-[(methylsulfonyl)amino]benzoate

Product 1

HCID 57762927ethyl 5-[(1R)-1-aminoethyl]-2-[(methylsulfonyl)amino]benzoateYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 5-((1R)-1-{[(R)-tert-butylsulfinyl]amino}ethyl)-2-[(methylsulfonyl)amino]benzoate (4.3 g,11 mmol) in methanol (30 ml) was added hydrogenchloride-methanol solution (30 ml). The solution was stirred at room temperature for 30 minutes and then concentrated under reduced pressure. The given residue was recrystallized from methanol-diethyl ether. The precipitate was then filtered, washed with diethyl ether and collected to furnish 3.1 g (87% yield) of the title compound as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe given residue was recrystallized from methanol-diethyl ether
  3. filtrationThe precipitate was then filtered
  4. washwashed with diethyl ether
  5. customcollected

Sources & evidence

ORD record
ord-03cf9079803349db97cb6c5dd4de1683
Source dataset
uspto-grants-2009_07
Patent number
US07566739B2

Reaction notes

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