Hydrogen Peroxide → 2-(R)-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acid

HRID 393704Notes

Reaction equation

HRID 393704 reaction equation
OO.C([C@@H]1COC(=O)N1[C:16](=[O:44])[C@H:17]([CH2:21][S:22]([N:25]1[CH2:30][CH2:29][N:28]([C:31]2[N:36]=[CH:35][C:34]([C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)=[CH:33][N:32]=2)[CH2:27][CH2:26]1)(=[O:24])=[O:23])[CH:18]([CH3:20])[CH3:19])C1C=CC=CC=1.O.[OH-].[Li+].S([O-])([O-])=[O:49].[Na+].[Na+]>O1CCCC1.O.[OH-].[Na+]>[F:43][C:40]1[CH:39]=[CH:38][C:37]([C:34]2[CH:35]=[N:36][C:31]([N:28]3[CH2:27][CH2:26][N:25]([S:22]([CH2:21][C@H:17]([CH:18]([CH3:19])[CH3:20])[C:16]([OH:49])=[O:44])(=[O:23])=[O:24])[CH2:30][CH2:29]3)=[N:32][CH:33]=2)=[CH:42][CH:41]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 168937Lithium hydroxide, monohydrateHCID 235197544-(R)-benzyl-3(2-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl)piperazine-1-sulfonylmethyl}-3-methylbutyryl)oxazolidin-2-one

Product 1

HCID 235197432-(R)-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acidYield 74%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Hydrogen peroxide (0.37 ml, 27.5 wt % in water) was added to an ice-cold solution of 4-(R)-Benzyl-3-(2-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyryl)oxazolidin-2-one(0.67 g) in tetrahydrofuran (5 ml), followed by the dropwise addition of a solution of lithium hydroxide monohydrate (61 mg) in water (2.5 ml), and the mixture stirred in the ice-bath, allowing to slowly warm to ambient temperature. After 4 h, the mixture was re-cooled in ice, treated with sodium sulfite (0.68 g) as a solution in water (15 ml), and stirred for 10 min. The mixture was then reduced in vacuo and the residue diluted with 1 M sodium hydroxide (10 ml) and washed with ethyl acetate (2×30 ml). The combined organic washes were back-extracted with 1M sodium hydroxide (2×10 ml), and the combined aqueous phase was acidified with citric acid to pH 3-4. The resultant suspension was filtered, and the solids washed with water and dried under vacuum at 40° C. to yield the title compound as a white solid (0.36 g, 74%).

Workup

  1. temperaturethe mixture was re-cooled in ice
  2. washwashed with ethyl acetate (2×30 ml)
  3. extractionThe combined organic washes were back-extracted with 1M sodium hydroxide (2×10 ml)
  4. filtrationThe resultant suspension was filtered
  5. washthe solids washed with water
  6. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-d6cbf1a3e39e4038bb45ce7584e6c6cf
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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