Diisopropylethylamine → N-[[1-[[[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexyl]carbonyl]-L-methioninal

HRID 1851854ノート

反応式

HRID 1851854 の反応式
C(N(CC)C(C)C)(C)C.[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[S:18][CH:19]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([NH:30][C:31]4([C:37]([NH:39][C@H:40]([CH2:45][OH:46])[CH2:41][CH2:42][S:43][CH3:44])=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)=[O:29])=[CH:24][CH:23]=3)[N:21]=2)[CH2:13][CH2:12]1>CS(C)=O.C(Cl)Cl>[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[S:18][CH:19]=[C:20]([C:22]3[CH:23]=[CH:24][C:25]([C:28]([NH:30][C:31]4([C:37]([NH:39][C@H:40]([CH:45]=[O:46])[CH2:41][CH2:42][S:43][CH3:44])=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)=[O:29])=[CH:26][CH:27]=3)[N:21]=2)[CH2:13][CH2:12]1

参加物

5

反応物 2

HCID 81531DiisopropylethylamineHCID 57672850N-[[1-[[[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexyl]carbonyl]-L-methioninol

生成物 1

HCID 57672869N-[[1-[[[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexyl]carbonyl]-L-methioninal収率 64.4%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

Under an argon gas atmosphere, 453 mg (3.5 mmol) of N,N-diisopropylethylamine was added dropwise to a solution of 658 mg (3.5 mmol) of sulfur trioxide-pyridine complex in 10 ml of anhydrous dimethyl sulfoxide and 5 ml of anhydrous methylene chloride under ice-cooling, and the mixture was stirred for 15 minutes. Further, under ice-cooling, a solution of 319 mg (0.58 mmol) of N-[[1-[[[4-[2-(4-methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexyl]carbonyl]-L-methioninol in 3 ml of anhydrous dimethyl sulfoxide was added to the reaction solution, and the mixture was stirred at the same temperature for 2 hours. The reaction solution was poured into ice-water, and the mixture was extracted with ethyl acetate twice. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and then saturated brine and dried with anhydrous magnesium sulfate. Thereafter, the solvent was distilled off under reduced pressure. 20 ml of diisopropyl ether was added to the residue, and the mixture was stirred at room temperature for 18 hours. The obtained crystal was collected by filtration to give 203 mg (64%) of the title compound.

後処理

  1. temperaturecooling
  2. temperatureFurther, under ice-cooling
  3. stirringthe mixture was stirred at the same temperature for 2 hours
  4. extractionthe mixture was extracted with ethyl acetate twice
  5. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution
  6. dry with materialsaturated brine and dried with anhydrous magnesium sulfate
  7. distillationThereafter, the solvent was distilled off under reduced pressure
  8. addition20 ml of diisopropyl ether was added to the residue
  9. stirringthe mixture was stirred at room temperature for 18 hours
  10. filtrationThe obtained crystal was collected by filtration

出典と根拠

ORDレコード
ord-e68c39162fb14fbcb1893f7bda0968cc
出典データセット
uspto-grants-2015_02
特許番号
US08957205B2

反応ノート

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