Sodium Acetate → (R)-2-Ethyl-6-trifluoromethyl-2,3-dihydro-1H-quinolin-4-one O-methyl-oxime

HRID 661458노트

반응식

HRID 661458 반응식
CS(O)(=O)=O.[CH2:6]([C@@H:8]1[CH2:17][C@H:16]([NH2:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[NH:9]1)[CH3:7].Cl.[CH3:24][O:25]N.C([O-])(=O)C.[Na+]>O.C1(C)C=CC=CC=1.O1CCCC1>[CH3:24][O:25][N:18]=[C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:19]([F:22])([F:20])[F:21])[CH:14]=2)[NH:9][C@H:8]([CH2:6][CH3:7])[CH2:17]1

참가 물질

7

반응물 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 86636540(2R,4S)-2-Ethyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinolin-4-ylamine methanesulfonate

생성물 1

HCID 136390757(R)-2-Ethyl-6-trifluoromethyl-2,3-dihydro-1H-quinolin-4-one O-methyl-oxime

시약·촉매·용매 3

HCID 962Water용매2회HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

The compound obtained in Example 2 (2) above (2.43 g), methoxyamine hydrochloride (1.25 g), sodium acetate (1.64 g) and water (2.4 ml) were added to tetrahydrofuran (22 ml) and the mixture was stirred at room temperature for about 48 hours. Toluene (24 ml) and water (12 ml) were added to the reaction mixture, the organic layer was separated, and washed with water (12 ml) and a saturated brine (12 ml). The organic layer was concentrated at reduced pressure and the resulting residue was purified by column chromatography and concentrated to give the titled compound as an oily material (1.92 g, yield 71%). MS (APCI) m/z: 273 [M+H]+.

후처리

  1. customthe organic layer was separated
  2. washwashed with water (12 ml)
  3. concentrationThe organic layer was concentrated at reduced pressure
  4. customthe resulting residue was purified by column chromatography
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-348f6dc224d64718b11e17756e2769de
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084611B2

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