Hydrogen Peroxide → 2-(R)-(3,4-Dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine-2-sulfonylmethyl)-3-methyl-butyric acid

HRID 1582043Notes

Reaction equation

HRID 1582043 reaction equation
OO.C([C@@H]1COC(=O)N1[C:16](=[O:38])[C@H:17]([CH2:21][S:22]([N:25]1[CH2:30][CH2:29][C:28]2[C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[S:33][C:27]=2[CH2:26]1)(=[O:24])=[O:23])[CH:18]([CH3:20])[CH3:19])C1C=CC=CC=1.O.[OH-].[Li+].S([O-])([O-])=[O:43].[Na+].[Na+]>O1CCCC1.O>[CH2:26]1[C:27]2[S:33][C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[C:28]=2[CH2:29][CH2:30][N:25]1[S:22]([CH2:21][C@H:17]([CH:18]([CH3:19])[CH3:20])[C:16]([OH:43])=[O:38])(=[O:23])=[O:24]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 168937Lithium hydroxide, monohydrateHCID 228882824(R)-Benzyl-3-[2-(R)-(3,4dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine-2-sulfonylmethyl)-3-methyl-butanoyl]-oxazolidin-2-one

Product 1

HCID 102703352-(R)-(3,4-Dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine-2-sulfonylmethyl)-3-methyl-butyric acidYield 87.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Hydrogen peroxide (30% aqueous, 0.15 ml) was added to a solution of 4-(R)-benzyl-3-[2-(R)-(3,4-dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine-2-sulfonylmethyl)-3-methyl-butanoyl]-oxazolidin-2-one (180 mg) in tetrahydrofuran (5 ml) at 0° C., followed by a solution of lithium hydroxide monohydrate (30 mg) in water (3 ml). The reaction was stirred for 16 h, allowing to warm slowly to room temperature. A solution of sodium sulfite (200 mg) in water (5 ml) was added then the mixture was evaporated under reduced pressure. The aqueous residue was washed with diethyl ether (20 ml), acidified with citric acid and extracted with ethyl acetate (2×30 ml). The combined extracts were washed with brine (30 ml), dried (MgSO4), filtered and evaporated under reduced pressure to give the title compound (110 mg) in crude form.

Workup

  1. customthe mixture was evaporated under reduced pressure
  2. washThe aqueous residue was washed with diethyl ether (20 ml)
  3. extractionextracted with ethyl acetate (2×30 ml)
  4. washThe combined extracts were washed with brine (30 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-42b7ced74fa141eda7b4f776deb43089
Source dataset
uspto-grants-2004_05
Patent number
US06734189B2

Reaction notes

Loading…