4-Nitrophenol → 4-Nitrophenyl 2-chloro-5-(pivalamidomethyl)benzoate

HRID 1469742노트

반응식

HRID 1469742 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CCN=C=NCCCN(C)C.[CH:30]1[C:35]([N+:36]([O-:38])=[O:37])=[CH:34][CH:33]=[C:32](O)[CH:31]=1.CCN(C(C)C)C(C)C>C1COCC1.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C:13](=[O:18])[C:14]([CH3:15])([CH3:17])[CH3:16])=[CH:7][C:3]=1[C:4]([O:6][C:32]1[CH:31]=[CH:30][C:35]([N+:36]([O-:38])=[O:37])=[CH:34][CH:33]=1)=[O:5]

참가 물질

7

반응물 4

HCID 9804-NitrophenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acid

생성물 1

HCID 866922384-Nitrophenyl 2-chloro-5-(pivalamidomethyl)benzoate수율 51.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-chloro-5-(pivalamidomethyl)benzoic acid (Intermediate-5, 300 mg, 1.12 mmol) in THF (5 mL) were added EDCI (210 mg, 1.09 mmol), p-nitrophenol (154 mg, 1.10 mmol) and DIPEA (558 mg, 4.39 mmol) and the reaction mixture was stirred at rt for 4 h. Then water was added to the reaction mixture and it was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 222 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.36 (d, J=9.0 Hz, 2H), 8.20 (t, 1H), 7.97 (s, 1H), 7.62-7.59 (m, 3H), 7.51 (d, J=8.1 Hz, 1H), 4.30 (d, J=6.0 Hz, 2H), 1.11 (s, 9H).

후처리

  1. extractionwas extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. customseparated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-6bb05300c02f40ada61cb67ca33ec74a
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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