Hydrochloric Acid → 2(R)-[(4-Fluoro-3-methylphenylsulfonyl)]amino-3-methylbutyric acid

HRID 1784953Notes

Reaction equation

HRID 1784953 reaction equation
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].C([O-])([O-])=O.[K+].[K+].[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][C:17]=1[CH3:26].Cl>O1CCOCC1.O.O1CCOCC1.C(OC(=O)C)C>[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:1][C@H:2]([CH:3]([CH3:5])[CH3:4])[C:6]([OH:8])=[O:7])(=[O:24])=[O:23])=[CH:18][C:17]=1[CH3:26]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 71563D-ValineHCID 27827584-Fluoro-3-methylbenzene-1-sulfonyl chloride

Product 1

HCID 422557322(R)-[(4-Fluoro-3-methylphenylsulfonyl)]amino-3-methylbutyric acid

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

D-Valine (1.39 g, 11.9 mmol) was dissolved in 80 ml of dioxane/water (1:1) containing K2CO3 (3.3 g, 24 mmol). A solution of 4-fluro-3-methylphenyl-sulfonylchloride (10 mmol) in dioxane (4 ml) was dropped in with good stirring. The reaction mixture was stirred at room temperature for 30 min. Ethylacetate (80 ml), 1N HCl (50 ml) was added. The organic layer was washed with 1N HCl 2 times, and extracted with 5% K2CO3 (3×25 ml). The combined base extracts was acidified and extracted with ethylaceate (80 ml). The organic layer was washed with brine (2×), dried over Na2SO4. The solvent was removed on rotavap, and residue tritrated with hexane. The resulting solid was dried to give 2(R)-[(4-fluoro-3-methylphenyl-sulfonyl)]amino-3-methylbutyric acid.

Workup

  1. washThe organic layer was washed with 1N HCl 2 times
  2. extractionextracted with 5% K2CO3 (3×25 ml)
  3. extractionextracted with ethylaceate (80 ml)
  4. washThe organic layer was washed with brine (2×)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed on rotavap
  7. customThe resulting solid was dried

Sources & evidence

ORD record
ord-c099c81471ed49b6a737d54bf864cdc4
Source dataset
uspto-grants-2009_03
Patent number
US07504425B2

Reaction notes

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