Beta-Alanine → 3-[(4-Hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acid

HRID 1480931ノート

反応式

HRID 1480931 の反応式
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[NH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27].CO>C[O-].[Na+]>[OH:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:11][CH:12]=2)[CH:7]=[N:6][C:5]=1[C:3]([NH:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:4]

参加物

5

反応物 3

HCID 239Beta-AlanineHCID 887MethanolHCID 86709142Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

生成物 1

HCID 717351373-[(4-Hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acid収率 89.1%

試薬・触媒・溶媒 1

HCID 10942334Sodium Methoxide溶媒

実験手順

A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (185 mg, 0.55 mmol), beta-alanine (489 mg, 5.5 mmol) in 0.5 M NaOMe in MeOH solution (8.8 mL, 4.4 mmol) was refluxed overnight. After cooled, the reaction mixture was concentrated and residue was dissolved in water (80 mL). It was acidified by 1 N HCl solution to pH ca. 3-4. Resulting gummy solid was collected by filtration, rinsed with water and then dissolved in EtOAc. The organic solution was dried over MgSO4, filtered and concentrated to provide the title compound (173 mg, 0.49 mmol) as an off-white solid in 89% yield. LC-MS ESI−: 351.14 (M−1)−.

後処理

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooled
  3. concentrationthe reaction mixture was concentrated
  4. dissolutionresidue was dissolved in water (80 mL)
  5. filtrationResulting gummy solid was collected by filtration
  6. washrinsed with water
  7. dissolutiondissolved in EtOAc
  8. dry with materialThe organic solution was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-216f22b7fe6742a38aae8e73d2589926
出典データセット
uspto-grants-2016_08
特許番号
US09409892B2

反応ノート

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