Ethanol → Ethyl (S)-[[1-(2-[[(1-amino-6-isoquinolinyl)carbonyl]amino]-1-oxopropyl)piperidin-4-yl]oxy]acetic acid hydrochloride

HRID 1279027ノート

反応式

HRID 1279027 の反応式
[ClH:1].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([NH:15][C@@H:16]([CH3:30])[C:17]([N:19]3[CH2:24][CH2:23][CH:22]([O:25][CH2:26][C:27]([OH:29])=[O:28])[CH2:21][CH2:20]3)=[O:18])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1.S(=O)(=O)(O)O.[OH-].[Na+].C(=O)([O-])O.[Na+].[CH2:43](O)[CH3:44]>[Cl-].[Na+].O.ClCCl>[ClH:1].[CH2:43]([C@H:26]([O:25][CH:22]1[CH2:21][CH2:20][N:19]([C:17](=[O:18])[CH:16]([NH:15][C:13]([C:9]2[CH:8]=[C:7]3[C:12](=[CH:11][CH:10]=2)[C:3]([NH2:2])=[N:4][CH:5]=[CH:6]3)=[O:14])[CH3:30])[CH2:24][CH2:23]1)[C:27]([OH:29])=[O:28])[CH3:44]

参加物

8

反応物 5

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 69780722(S)-[[1-(2-[[(1-amino-6-isoquinolinyl)carbonyl]amino]-1-oxopropyl)piperidin-4-yl]oxy]acetic acid hydrochloride

生成物 1

HCID 86758500Ethyl (S)-[[1-(2-[[(1-amino-6-isoquinolinyl)carbonyl]amino]-1-oxopropyl)piperidin-4-yl]oxy]acetic acid hydrochloride

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a stirred solution of 394 mg of (S)-[[1-(2-[[(1-amino-6-isoquinolinyl)carbonyl]amino]-1-oxopropyl)piperidin-4-yl]oxy]acetic acid hydrochloride in 10 mL of ethanol at 0° C. was added 0.55 mL of sulfuric acid (95-98%). The reaction mixture was allowed to warm to room temperature and after 2 hours 5 mL of 2N aqueous sodium hydroxide, 20 mL of brine, 20 mL of 5% aqueous sodium hydrogencarbonate and 40 mL of dichloromethane was added. The organic layer was separated and the aqueous layer was extracted three times with dichloromethane. The combined organic layers were dried (sodium sulfate) and concentrated. Purification using column chromatography (silica gel, dichloromethane:ethanol =9:1) and lyophilisation (t-butanol/hydrochloric acid) yielded 265 mg of the title compound.

後処理

  1. additionwas added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted three times with dichloromethane
  4. dry with materialThe combined organic layers were dried (sodium sulfate)
  5. concentrationconcentrated
  6. customPurification

出典と根拠

ORDレコード
ord-2f2e6c15f92d46958dbdbc88bea329bd
出典データセット
uspto-grants-2002_09
特許番号
US06444672B1

反応ノート

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