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 1072626

반응식

HRID 1072626 반응식
[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]

참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a solution of 3-[1-[2-amino-3-(4-fluorophenyl)propionyl]-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.

후처리

  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

출처 및 근거

ORD 기록
ord-80c54747813c4fc0ad506ec87eafe1b5
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06911447B2

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