Hydrochloric Acid → 6-(3-Chloro-4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylic acid

HRID 1817334ノート

反応式

HRID 1817334 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:22][CH3:23])[C:10](=[O:21])[N:11]([CH3:20])[C:12]=2[C:16]([O:18]C)=[O:17])[C:7]1=[O:24].[Li+].[OH-].Cl>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:22][CH3:23])[C:10](=[O:21])[N:11]([CH3:20])[C:12]=2[C:16]([OH:18])=[O:17])[C:7]1=[O:24]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69058384Methyl 6-(3-chloro-4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate

生成物 1

HCID 690633856-(3-Chloro-4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylic acid

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a solution of methyl 6-(3-chloro-4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate (14.3 g, 35 mmol) in THF (1501 mL) and MeOH (150 mL) was added LiOH (2.74 g, 114 mmol) dissolved in 114 mL water and the reaction was heated to 50° C. for 45 minutes. HPLC showed completion. The reaction was neutralized with 1N HCl and cooled to room temperature. THF was removed in vacuo, and the resulting slurry was partitioned between CHCl3 and 5% aqueous HCl. The aqueous was washed with additional CHCl3. The combined organics were dried over sodium sulfate, filtered, and concentrated to dryness to afford the desired product as a pale yellow foam. The material was crystallized from ethyl acetate to give a light yellow solid.

後処理

  1. temperaturecooled to room temperature
  2. customTHF was removed in vacuo
  3. customthe resulting slurry was partitioned between CHCl3 and 5% aqueous HCl
  4. washThe aqueous was washed with additional CHCl3
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-8180ba4d769c41049f5223035641027a
出典データセット
uspto-grants-2009_10
特許番号
US07598264B2

反応ノート

読み込み中…