Sodium Glycinate → [(1-Benzyl-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-acetic acid

HRID 919674

反応式

HRID 919674 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][C:26]([O-:28])=[O:27].[Na+]>COCCO>[CH2:15]([N:11]1[C:12]2[C:7](=[C:6]([OH:23])[C:5]([C:3]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[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 2

HCID 4684308Sodium GlycinateHCID 682974351-Benzyl-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

生成物 1

HCID 60152772[(1-Benzyl-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-acetic acid収率 74.3%

試薬・触媒・溶媒 1

HCID 80192-Methoxyethanol溶媒

実験手順

A mixture of 1-benzyl-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (100 mg, 0.32 mmol) and sodium glycinate (626 mg, 6.45 mmol) in 2-methoxyethanol (10 mL) was refluxed for 2 h. The solvent was evaporated in vacuo, and the residue was dissolved in saturated NaHCO3. The aqueous phase was washed with ether, and then acidified to pH about 2 with 4M HCl. The resulting suspension was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give 84 mg of the title compound as a pale yellow solid. MS: (+) m/z 354.02 (M+1).

後処理

  1. temperaturewas refluxed for 2 h
  2. customThe solvent was evaporated in vacuo
  3. dissolutionthe residue was dissolved in saturated NaHCO3
  4. washThe aqueous phase was washed with ether
  5. extractionThe resulting suspension was extracted with EtOAc
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-f56091ddf44643939d35260a9030d6ea
出典データセット
uspto-grants-2016_03
特許番号
US09271970B2

関連ノート

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