Hydrochloric Acid → 2-(4-tert-butoxycarbonylbenzyl)-6-dimethylcarbamoyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750258ノート

反応式

HRID 750258 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:28][CH:27]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([C:21]([OH:23])=O)=[CH:10][CH:9]=2)=[O:4].[Cl-].C[NH3+].Cl.[CH2:43]([N:45]=[C:46]=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.Cl>C1COCC1.O.C(N(CC)CC)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:30][CH:31]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([C:21](=[O:23])[N:45]([CH3:46])[CH3:43])=[CH:10][CH:9]=2)=[O:4]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 11637Methanamine, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 691566122-(4-tert-butoxycarbonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic Acid 3-methyl Ester

生成物 1

HCID 691567922-(4-tert-butoxycarbonylbenzyl)-6-dimethylcarbamoyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester収率 50.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

反応条件

温度
40 °C

実験手順

To a solution of 2-(4-tert-butoxycarbonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic acid 3-methyl ester (300 mg) in THF (6 ml) were added methyl ammonium chloride (150 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (230 mg), 1-hydroxy-1H-benzotriazole monohydrate (180 mg) and triethylamine (1 ml) at room temperature. The reaction mixture was stirred at 40° C. for 12 hrs. Water and 1N-hydrochloric acid were added to acidify the aqueous layer and the mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was crystallized from methanol to give the title compound (160 mg).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was crystallized from methanol

出典と根拠

ORDレコード
ord-68c381e626cf4d3abedf78cffd75543a
出典データセット
uspto-grants-2008_07
特許番号
US07402595B2

反応ノート

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