Sodium ethoxide → HCID 69481040、化合物

HRID 2364530ノート

反応式

HRID 2364530 の反応式
[CH:1]1([N:4]([C:23](=[O:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:5]2[C:6]([C:19]([O:21]C)=O)=[N:7][CH:8]=[C:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:10]=2)[CH2:3][CH2:2]1.[O-]CC.[Na+]>C(O)C>[CH:1]1([N:4]2[C:5]3[C:6](=[N:7][CH:8]=[C:9]([CH2:11][C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)[CH:10]=3)[C:19]([OH:21])=[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:23]2=[O:30])[CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 2723922Sodium ethoxideHCID 69480475Methyl 3-{cyclopropyl[3-(ethyloxy)-3-oxopropanoyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate

生成物 1

HCID 69481040HCID 69481040、化合物収率 98%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of methyl 3-{cyclopropyl[3-(ethyloxy)-3-oxopropanoyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (402 mg, 0.97 mmol) in ethanol (20 mL) at 0° C. was treated with sodium ethoxide (165 mg, 2.4 mmol). The reaction mixture was allowed to warm to room temperature as the bath warmed overnight. Solvents were removed in vacuo and the residue was taken up in water. The pH was adjusted to ˜5 with 1 N HCl (aq) and the aqueous layer extracted with ethyl acetate. The organics were dried over sodium sulfate filtered and concentrated to give ethyl 1-cyclopropyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (362 mg, 98%) as a solid. 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=1.6 Hz, 1 H), 7.78 (s, 1 H), 7.18 (dd, J=8.7, 5.4 Hz, 2 H), 7.04 (t, J=8.7 Hz, 2 H), 4.50 (q, J=7.1 Hz, 2 H), 4.13 (s, 2 H), 2.77 (m, 1 H), 1.46 (t, J=7.3 Hz, 3 H), 1.22 (m, 2 H), 0.76 (m, 2 H); MS m/z 383 (M+1).

後処理

  1. temperaturewarmed overnight
  2. customSolvents were removed in vacuo
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-1f0de86dc7cd404f817e7b0afb071e09
出典データセット
uspto-grants-2014_04
特許番号
US08691991B2

反応ノート

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