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

HRID 1469709ノート

反応式

HRID 1469709 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-83ffd3354fad4a3a8255618d57d452b5
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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