1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[(2S,3S)-2-hydroxy-1-[N-(butyl)amino]-1-oxo-3-heptyl]-1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxamide

HRID 2053478ノート

反応式

HRID 2053478 の反応式
[CH2:1]([NH:5][C:6](=[O:15])[C@@H:7]([OH:14])[C@@H:8]([NH2:13])[CH2:9][CH2:10][CH2:11][CH3:12])[CH2:2][CH2:3][CH3:4].[N:16]1([C:22]([NH:24][C:25]2([C:31](O)=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>ClCCl>[OH:14][C@@H:7]([C@@H:8]([NH:13][C:31]([C:25]1([NH:24][C:22]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:23])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1)=[O:32])[CH2:9][CH2:10][CH2:11][CH3:12])[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:15]

参加物

6

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 115071371-(Morpholine-4-carboxamido)cyclohexanecarboxylic acidHCID 59655570(2S,3S)-N-butyl-3-amino-2-hydroxyheptanamide

生成物 1

HCID 53630496N-[(2S,3S)-2-hydroxy-1-[N-(butyl)amino]-1-oxo-3-heptyl]-1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxamide収率 89%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In anhydrous dichloromethane were dissolved 254 mg (1.21 mmol) of (2S,3S)-N-butyl-3-amino-2-hydroxyheptanamide, 310 mg (1.21 mmol) of 1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxylic acid and 230 mg (1.45 mmol) of 1-hydroxybenzotriazole, subsequently, under nitrogen stream, 278 mg (1.45 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide was added to the solution at 0° C. Thereafter, the temperature of the reaction mixture was returned to room temperature and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in 80 ml of ethyl acetate, and the resulting mixture was washed successively with water, a 10% aqueous potassium hydrogen sulfate solution, a saturated aqueous sodium hydrogen carbonate solution and a saturated NaCl solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 489 mg (Yield: 89%) of the desired compound.

後処理

  1. customwas returned to room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in 80 ml of ethyl acetate
  4. washthe resulting mixture was washed successively with water
  5. dry with materiala 10% aqueous potassium hydrogen sulfate solution, a saturated aqueous sodium hydrogen carbonate solution and a saturated NaCl solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-02843ff2ba62494cac839ad8ba0c6e4e
出典データセット
uspto-grants-2008_02
特許番号
US07326799B2

反応ノート

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