4-Methylmorpholine → 2-acetylamino-N-[2-[2-(2-cyanoethyl)-4-(2-naphthalen-2-ylethyl)-5-oxo-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethyl]-3-(4-hydroxyphenyl)-propionamide

HRID 8526

反応式

HRID 8526 の反応式
[NH2:1][CH:2]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)[C:3]([N:5]1[CH2:10][C:9](=[O:11])[N:8]([CH2:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:7][CH:6]1[CH2:24][CH2:25][C:26]#[N:27])=[O:4].[C:36]([NH:39][C@H:40]([C:49](O)=[O:50])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([OH:48])=[CH:44][CH:43]=1)(=[O:38])[CH3:37].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.CN(C)CCCN=C=NCC>CN(C=O)C.O>[C:36]([NH:39][CH:40]([CH2:41][C:42]1[CH:43]=[CH:44][C:45]([OH:48])=[CH:46][CH:47]=1)[C:49]([NH:1][CH:2]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)[C:3]([N:5]1[CH2:10][C:9](=[O:11])[N:8]([CH2:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:7][CH:6]1[CH2:24][CH2:25][C:26]#[N:27])=[O:4])=[O:50])(=[O:38])[CH3:37]

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68310N-Acetyl-L-tyrosineHCID 757711-HydroxybenzotriazoleHCID 220156953-[1-[2-Amino-3-(4-fluorophenyl)propionyl]-4-(2-naphthalen-2-ylethyl)-5-oxo-piperazin-2-yl]propionitrile

生成物 1

HCID 220156872-acetylamino-N-[2-[2-(2-cyanoethyl)-4-(2-naphthalen-2-ylethyl)-5-oxo-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethyl]-3-(4-hydroxyphenyl)-propionamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of 3-[1-[2-amino-3-(4-fluorophenyl)proponyl]-4-(2-naphthalen-2-ylethyl)-5-oxo-piperazin-2-yl]propionitrile, 33, (47.2 g, 100 mmol), N-acetyl-L-tyrosine (22.3 g, 120 mmol), 1-hydroxybenzotriazole (16.2 g, 120 mmol), and N-methylmorpholine (132 mL, 120 mmol) in DMF (150 mL) is cooled to 0° C. and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (24.9 g, 130 mmol) is slowly added. The resulting mixture is stirred for 2 hours at 0° C. then allowed to warm and stir at room temperature another 2 hours. The reaction solution is diluted with water and the resulting solid is collected by filtration, re-dissolved in EtOAc and extracted with water, dried and concentrated in vacuo to afford the crude product which is purified over silica gel.

後処理

  1. temperatureto warm
  2. stirringstir at room temperature another 2 hours
  3. filtrationthe resulting solid is collected by filtration
  4. dissolutionre-dissolved in EtOAc
  5. extractionextracted with water
  6. customdried
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8bd411e3c3ab4b63b8ed399336f16009
出典データセット
uspto-grants-2006_08
特許番号
US07087759B2

関連ノート

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