Beta-Alanine → 3-[(1-Benzyl-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-propionic acid

HRID 1410847ノート

反応式

HRID 1410847 の反応式
CO[C:3]([C:5]1[C:6]([OH:23])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[CH:9]=[CH:8]2)=[O:4].[NH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28].C[O-].[Na+]>>[CH2:15]([N:11]1[C:12]2[C:7](=[C:6]([OH:23])[C:5]([C:3]([NH:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:4])=[N:14][CH:13]=2)[CH:8]=[CH:9][C:10]1=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

4

反応物 3

HCID 239Beta-AlanineHCID 10942334Sodium MethoxideHCID 682974351-Benzyl-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

生成物 1

HCID 601515403-[(1-Benzyl-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-propionic acid収率 69.1%

実験手順

A mixture of 1-benzyl-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (40 mg, 0.13 mmol), β-alanine (920 mg, 10.3 mmol) and NaOMe solution (15 mL, 7.7 mmol, 0.5 M in MeOH) was refluxed for 16 h. The solvent was evaporated in vacuo, and the residue was dissolved in water and washed several times with ether. The aqueous layer was acidified to pH about 2 with 4 M HCl, and the resulting precipitate was collected by filtration and dried to give 33 mg of the title compound as an off-white solid. MS: (+) m/z 368.24 (M+1).

後処理

  1. temperaturewas refluxed for 16 h
  2. customThe solvent was evaporated in vacuo
  3. dissolutionthe residue was dissolved in water
  4. washwashed several times with ether
  5. filtrationthe resulting precipitate was collected by filtration
  6. customdried

出典と根拠

ORDレコード
ord-c53f7a8e1487475d99fcf027ee6c4178
出典データセット
uspto-grants-2014_12
特許番号
US08921389B2

反応ノート

読み込み中…