Hydrochloric Acid → 3-[(1-Cyano-4-hydroxy-7-phenethyl-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid

HRID 1481138ノート

反応式

HRID 1481138 の反応式
C[O:2][C:3](=[O:32])[C:4]([CH3:31])([CH3:30])[CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]([C:28]#[N:29])[C:12]2[C:17]([C:18]=1[OH:19])=[CH:16][CH:15]=[C:14]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:13]=2)=[O:8].[OH-].[Na+].Cl>CO>[C:28]([C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[C:14]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:13]=2)[C:18]([OH:19])=[C:9]([C:7]([NH:6][CH2:5][C:4]([CH3:31])([CH3:30])[C:3]([OH:32])=[O:2])=[O:8])[N:10]=1)#[N:29]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 898130143-[(1-Cyano-4-hydroxy-7-phenethyl-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid methyl ester

生成物 1

HCID 717359453-[(1-Cyano-4-hydroxy-7-phenethyl-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid収率 70%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 3-[(1-cyano-4-hydroxy-7-phenethyl-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid methyl ester (55 mg, 0.13 mmol), 2 M NaOH (2 mL) and MeOH (2 mL) was stirred at r.t. for 3 h. 1 M HCl was added until pH was ˜2, and the resulting suspension was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography (0-30% EtOAc/hexanes+2% AcOH) to give 38 mg of the title compound. MS: (−) m/z 416.14 (M−1).

後処理

  1. extractionthe resulting suspension was extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (0-30% EtOAc/hexanes+2% AcOH)

出典と根拠

ORDレコード
ord-3b969af328634b3ba330d01803a61fe6
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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