Hydrochloric Acid → 3-[4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic Acid

HRID 1832055ノート

反応式

HRID 1832055 の反応式
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=2[CH3:23])[C:16]([O:18]C)=[O:17])[C:8](=[O:24])[CH:7]=1.[OH-].[Na+].Cl>C1COCC1.O>[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=2[CH3:23])[C:16]([OH:18])=[O:17])[C:8](=[O:24])[CH:7]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22050431HCID 22050431、化合物

生成物 1

HCID 220503253-[4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic Acid収率 66.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 3-[4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoate (14 g, 35.0 mmol) (from step 2) was taken up in THF (25 ml) and H2O. 2.5 N NaOH (aq.) was added and the reaction stirred for 30 minutes at room temperature. The reaction was made acidic via the addition of concentrated HCl. The product was extracted with ethyl acetate. The ethyl acetate extraction was dried over Na2SO4, filtered, and the solvent removed in vacuo. Upon vacuum removal of the solvent, the product crashed out of the ethyl acetate. This precipitate was collected on a filter pad and washed with a 50 ethyl acetate/hexanes to yield a white powder (9 g, 7%). 1H NMR (300 MHz, CDCl3) δ 8.01 (dd, J=, 1.61 Hz, 1H), 7.84 (d, J=1.61 Hz, 1H), 7.52-7.47 (app q, J=8.26, 1H), 7.43 (d, J=8.06 Hz, 1H), 7.00-6.88 (m, 2H), 6.19 (d, J=2.62 Hz, 1H), 6.05 (dd, J=2.62, 1.81 Hz, 1H), 5.17 (s, 2H), 2.19 (s, 3H), 1.90 (s, 3H); ES-HR/MS m/z 386.12 (M+H calcd for C21H18F2NO4 requires 386.1198).

後処理

  1. extractionThe product was extracted with ethyl acetate
  2. extractionThe ethyl acetate extraction
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customUpon vacuum removal of the solvent
  7. customThis precipitate was collected on a filter pad
  8. washwashed with a 50 ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-4c6f36aab9c4463ba8a6d83f52b2dd81
出典データセット
uspto-grants-2006_06
特許番号
US07067540B2

反応ノート

読み込み中…