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

HRID 1784953노트

반응식

HRID 1784953 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c099c81471ed49b6a737d54bf864cdc4
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504425B2

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