Triethylamine → Ethyl 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoate

HRID 1469709노트

반응식

HRID 1469709 반응식
[NH2:1][CH2:2][C:3]1[C:4]([F:15])=[C:5]([C:11]([Cl:14])=[CH:12][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].CCN(CC)CC.[C:23](Cl)(=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25]>C1COCC1.CCOC(C)=O>[Cl:14][C:11]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([F:15])[C:3]([CH2:2][NH:1][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:13][CH:12]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 58483233Ethyl 3-(aminomethyl)-6-chloro-2-fluorobenzoate

생성물 1

HCID 58483442Ethyl 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoate수율 73.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of ethyl 3-(aminomethyl)-6-chloro-2-fluorobenzoate (70 mg, 0.3 mmol) in THF (3 mL) were added Et3N (0.105 mL, 0.76 mmol) and pivaloyl chloride (38 μL, 0.31 mmol). The reaction mass was stirred at rt for 2 h, 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 8.15 (br t, 1H), 7.43-7.35 (m, 2H), 4.38 (q, J=7.2 Hz, 2H), 4.26 (d, J=5.7 Hz, 2H), 1.30 (t, J=6.9 Hz, 3H), 1.11 (s, 9H).

후처리

  1. washwas washed with water, and brine
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-83ffd3354fad4a3a8255618d57d452b5
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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