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

HRID 1480931노트

반응식

HRID 1480931 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 10942334Sodium Methoxide용매

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-216f22b7fe6742a38aae8e73d2589926
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409892B2

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