Glycine → 2-(1-Cyano-4-hydroxyisoquinoline-3-carboxamido)acetic acid

HRID 2077114ノート

反応式

HRID 2077114 の反応式
C(O[C:6]([C:8]1[N:9]=[C:10]([C:19]#[N:20])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:21][CH2:22][C:23]([OH:25])=[O:24].CO[Na].CO>>[C:19]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:7])[N:9]=1)#[N:20]

参加物

5

反応物 4

HCID 750GlycineHCID 887MethanolHCID 671101221-Cyano-4-hydroxy-isoquinoline-3-carboxylic acid butyl esterHCID 178418582HCID 178418582、化合物

生成物 1

HCID 247799862-(1-Cyano-4-hydroxyisoquinoline-3-carboxamido)acetic acid収率 80.4%

実験手順

A mixture of 1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (89 mg, 0.33 mmol), glycine (375 mg, 5 mmol), and a 0.5 N solution of MeONa in MeOH (8 mL, 4 mmol) was refluxed with stirring for 48 h before it was concentrated in vacuo. The residue was dissolved in water (20 mL). The solution was washed with diethyl ether before its pH was adjusted to 2 to 3 by addition of aqueous 6 N HCl. The resulting suspension was extracted with ethyl acetate (1×30 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a yellowish solid (72 mg); MS-(−)-ion: M−1=270.2.

後処理

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe residue was dissolved in water (20 mL)
  3. washThe solution was washed with diethyl ether before its pH
  4. additionwas adjusted to 2 to 3 by addition of aqueous 6 N HCl
  5. extractionThe resulting suspension was extracted with ethyl acetate (1×30 mL)
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e92993702f1c4e7bbac172206828b7cc
出典データセット
uspto-grants-2011_04
特許番号
US07928120B2

反応ノート

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