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

HRID 992434
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HRID 992434 반응식
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]
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참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ebb8c583561540cba3c6d8267b77d1c0
출처 데이터셋
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06469020B2

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