Diisopropylethylamine → HCID 68470489、化合物

HRID 1929307ノート

反応式

HRID 1929307 の反応式
[NH2:1][CH:2]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]([CH3:15])[C:3]1=[O:16].[C:17]([O:21][C:22]([NH:24][C@H:25]([C:27](O)=[O:28])[CH3:26])=[O:23])([CH3:20])([CH3:19])[CH3:18].O.OC1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>O.ClCCl>[C:17]([O:21][C:22](=[O:23])[NH:24][C@H:25]([C:27](=[O:28])[NH:1][CH:2]1[CH:8]=[C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][N:4]([CH3:15])[C:3]1=[O:16])[CH3:26])([CH3:18])([CH3:19])[CH3:20]

参加物

8

反応物 5

HCID 81531DiisopropylethylamineHCID 85082Tert-butoxycarbonylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 573467493-Amino-1-methyl-5-phenyl-1,3-dihydro-2H-azepin-2-oneHCID 178526939HCID 178526939、化合物

生成物 1

HCID 68470489HCID 68470489、化合物収率 97%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
10 °C

実験手順

3-Amino-1-methyl-5-phenyl-1,3-dihydro-azepin-2-one (330 g, 1.54 mol) is combined with dichloromethane (3 L), N-(tert-butoxycarbonyl)-L-alanine (291.4 g, 1.54 mol), and hydroxybenzotriazole hydrate (259.5 g, 1.617 mol). The solution is cooled to about 10° C. To this solution is added diisopropylethylamine (335.4 mL, 1.925 mol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (310.1 g, 1.617 mol) and the contents are allowed to gradually warm to room temperature. After 3.5 hours, the reaction contents are poured into water (1000 mL) and the layers are allowed to separate. The organic layer is further washed with water (1000 mL), 0.1 N HCl (1000 mL), saturated NaHCO3 solution (1000 mL) and finally saturated aqueous sodium chloride solution. The dichloromethane layer is dried over Na2SO4, filtered, and concentrated via rotary evaporation to provide the title compound (about 574 g, 97%) as a tan foam. The material is of sufficient purity to use directly in the next step.

後処理

  1. temperatureto gradually warm to room temperature
  2. customthe reaction contents
  3. customto separate
  4. washThe organic layer is further washed with water (1000 mL), 0.1 N HCl (1000 mL), saturated NaHCO3 solution (1000 mL) and finally saturated aqueous sodium chloride solution
  5. dry with materialThe dichloromethane layer is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated via rotary evaporation

出典と根拠

ORDレコード
ord-85745c656adc4f738dabd64eda702fee
出典データセット
uspto-grants-2012_05
特許番号
US08188069B2

反応ノート

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