Beta-Alanine → 3-[(6-Benzyl-4-hydroxy-5-oxo-5,6-dihydro-[2,6]naphthyridine-3-carbonyl)-amino]-propionic acid

HRID 1410759노트

반응식

HRID 1410759 반응식
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[CH:9]=[CH:10][N:11]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12](=[O:16])[C:13]=2[C:14]=1[OH:15])=[O:4].[NH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28].C[O-].[Na+]>>[CH2:17]([N:11]1[CH:10]=[CH:9][C:8]2[CH:7]=[N:6][C:5]([C:3]([NH:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:4])=[C:14]([OH:15])[C:13]=2[C:12]1=[O:16])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

4

반응물 3

HCID 239Beta-AlanineHCID 10942334Sodium MethoxideHCID 68297693Methyl 6-benzyl-4-hydroxy-5-oxo-5,6-dihydro-2,6-naphthyridine-3-carboxylate

생성물 1

HCID 682975893-[(6-Benzyl-4-hydroxy-5-oxo-5,6-dihydro-[2,6]naphthyridine-3-carbonyl)-amino]-propionic acid수율 67.2%

실험 절차

A mixture of 6-benzyl-4-hydroxy-5-oxo-5,6-dihydro-[2,6]naphthyridine-3-carboxylic acid methyl ester (25 mg, 0.081 mmol), β-alanine (956 mg, 10.7 mmol) and NaOMe solution (16 mL, 8.06 mmol, 0.5 M in MeOH) was refluxed for 16 h. Solvent was evaporated in vacuo, and the residue was partitioned between water and EtOAc. 1 M HCl was added with vigorous stirring until pH was about 2. The organic layer was dried over MgSO4 and concentrated. The crude solid was dissolved in saturated NaHCO3 and washed with ether. The aqueous layer was acidified to pH about 2 with 4 M HCl, and then extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give 20 mg of the title compound. MS: (+) m/z 368.00 (M+1).

후처리

  1. temperaturewas refluxed for 16 h
  2. customSolvent was evaporated in vacuo
  3. customthe residue was partitioned between water and EtOAc
  4. addition1 M HCl was added
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. dissolutionThe crude solid was dissolved in saturated NaHCO3
  8. washwashed with ether
  9. extractionextracted with EtOAc
  10. dry with materialThe organic layer was dried over MgSO4
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5a19f2383b0c4ac3a8846951cc5b03bd
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921389B2

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