Citric Acid → 6-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid

HRID 1469710노트

반응식

HRID 1469710 반응식
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([F:13])[C:5]([CH2:14][NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO.O>[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([F:13])[C:5]([CH2:14][NH:15][C:16](=[O:21])[C:17]([CH3:19])([CH3:18])[CH3:20])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 58483442Ethyl 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoate

생성물 1

HCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid수율 76.7%

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

To a solution of ethyl 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoate (100 mg, 0.317 mmol) in THF:MeOH:H2O (3:2:1; 6 mL) was added NaOH (25 mg, 0.634 mmol). The reaction mass was stirred at rt 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 70 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 14.10 (s, 1H), 8.14 (br t, 1H), 7.38-7.26 (m, 2H), 4.25 (d, J=5.4 Hz, 2H), 1.11 (s, 9H).

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-16a8d297a87244c49822f746c5a96586
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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