Citric Acid → HCID 71678385, 화합물

HRID 1469773노트

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HRID 1469773 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 71678385HCID 71678385, 화합물

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

반응 조건

온도
100 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-c92a8b68a5a14c679b89bb441e37ae03
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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