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

HRID 661458ノート

反応式

HRID 661458 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-348f6dc224d64718b11e17756e2769de
出典データセット
uspto-grants-2011_12
特許番号
US08084611B2

反応ノート

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