Beta-Alanine → 3-[(4-Hydroxy-1-methyl-7 phenoxy-isoquinoline-3-carbonyl)-amino]-propionic acid

HRID 1481117

反応式

HRID 1481117 の反応式
CO[C:3]([C:5]1[N:6]=[C:7]([CH3:23])[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].[NH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28].C[O-].[Na+].CO>>[OH:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:11][CH:12]=2)[C:7]([CH3:23])=[N:6][C:5]=1[C:3]([NH:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:4]

参加物

4

反応物 3

HCID 239Beta-AlanineHCID 23694274Sodium methanolate methanolHCID 712448953-Isoquinolinecarboxylic acid, 4-hydroxy-1-methyl-7-phenoxy-, methyl ester

生成物 1

HCID 898128553-[(4-Hydroxy-1-methyl-7 phenoxy-isoquinoline-3-carbonyl)-amino]-propionic acid収率 82.1%

実験手順

A mixture of 4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (120 mg, 0.39 mmol) and beta-alanine (242 mg, 2.72 mmol) in 0.5 M NaOMe/MeOH solution (4.5 mL, 2.25 mmol) was microwaved at 120° C. for 30 min. Reaction mixture was concentrated and dissolved in water (100 mL). It was acidified by 1 N HCl to pH=3-4. Gummy precipitate was collected by filtration and dissolved in EtOAc. It was dried over MgSO4, filtered and concentrated to provide the title compound 116 mg (0.32 mmol) in 81% yield. LC-MS ESI−: 365.16 (M−1)−.

後処理

  1. customwas microwaved at 120° C. for 30 min
  2. customReaction mixture
  3. concentrationwas concentrated
  4. dissolutiondissolved in water (100 mL)
  5. filtrationGummy precipitate was collected by filtration
  6. dissolutiondissolved in EtOAc
  7. dry with materialIt was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-a8b543e6e47b4103b198a565651bca07
出典データセット
uspto-grants-2016_08
特許番号
US09409892B2

関連ノート

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