Citric Acid → HCID 71678385、化合物

HRID 1469773ノート

反応式

HRID 1469773 の反応式
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6](F)[C:5]([CH2:14][NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:4][CH:3]=1.[OH-].[K+].C(O)(=O)C[C:26](CC(O)=O)(C(O)=O)[OH:27]>C1COCC1.CO.O>[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([O:27][CH3:26])[C:5]([CH2:14][NH:15][C:16](=[O:21])[C:17]([CH3:18])([CH3:19])[CH3:20])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 311Citric AcidHCID 14797Potassium HydroxideHCID 58483442Ethyl 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoate

生成物 1

HCID 71678385HCID 71678385、化合物

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

反応条件

温度
100 °C

実験手順

To a solution of ethyl 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoate (Intermediate-2; step-2, 1.00 g, 3.31 mmol) in THF:MeOH:H2O (2:2:1; 5 mL) was added KOH (930 mg, 16.57 mmol). The reaction mass was heated in a sealed tube at 100° C. for 3 h. The reaction mass was neutralized with citric acid and concentrated. The residue was diluted with EtOAc and was washed with water and brine. The organic layer was separated, dried, filtered and concentrated to afford 700 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 13.65 (br s, 1H), 8.08 (t, 1H), 7.29-7.26 (d, J=8.4 Hz, 1H), 7.22-7.19 (d, J=8.7 Hz, 1H), 4.25 (d, J=5.7 Hz, 2H), 3.79 (s, 3H), 1.13 (s, 9H); MS (m/z): 300.05 (M+H)+.

後処理

  1. concentrationconcentrated
  2. additionThe residue was diluted with EtOAc
  3. washwas washed with water and brine
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-c92a8b68a5a14c679b89bb441e37ae03
出典データセット
uspto-grants-2015_04
特許番号
US09006257B2

反応ノート

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