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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → methyl (5R)-3-[4-(1,1-dioxido-2,3-dihydro-4H-1,4-thiazin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinecarboxylate

HRID 723886
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HRID 723886 반응식
[O:1]=[S:2]1(=[O:26])[CH2:7][CH2:6][N:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([N:15]3[CH2:19][C@H:18]([C:20]([O:22][CH3:23])=[O:21])[O:17][C:16]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4][CH2:3]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[O-]S([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[O:26]=[S:2]1(=[O:1])[CH:3]=[CH:4][N:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([N:15]3[CH2:19][C@H:18]([C:20]([O:22][CH3:23])=[O:21])[O:17][C:16]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:6][CH2:7]1
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참가 물질

6

반응물 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 24437Sodium SulfiteHCID 68489310methyl (5R)-3-[4-(1,1-dioxidothiomorpholin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinecarboxylate

생성물 1

HCID 68490087methyl (5R)-3-[4-(1,1-dioxido-2,3-dihydro-4H-1,4-thiazin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinecarboxylate수율 38.6%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 312751,4-Dioxane용매

실험 절차

A solution of methyl (5R)-3-[4-(1,1-dioxidothiomorpholin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinecarboxylate (Step 2, 0.73 g, 1.87 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (1.27 g, 5.6 mmol) in dioxane (9 mL) is heated to 100° C. for two days. The solution is cooled and treated with 20 mL of 10% aqueous Na2SO3 and stirred for 30 minutes. The solution is then diluted with water and extracted three times with ethyl acetate. The combined organic phases are washed with satd NaHCO3 and saline and dried (MgSO4), filtered and concentrated. The crude residue is purified by column chromatography (0→5% ethyl ether-dichloromethane) to provide the title compound (0.28 g, 38%); 1H NMR (300 MHz, CDCl3): δ 3.31–3.35 (m, 2H), 3.89 (s, 3H), 4.00–4.15 (m, 3H), 4.25 (t, 1H), 5.11 (m, 1H), 5.45 (d, 1H), 6.54 (d, 1H), 7.29 (d, 2H).

후처리

  1. temperatureThe solution is cooled
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic phases are washed with satd NaHCO3 and saline
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue is purified by column chromatography (0→5% ethyl ether-dichloromethane)

출처 및 근거

ORD 기록
ord-d82071b54f164329a1053632478a2495
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07141588B2

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