Triethylamine → (S)-3-[4-(2,6-Dichlorobenzoylamino)phenyl]-2-{3-[2-(toluene-4-sulfonyl)-5-trifluoro methylphenyl]ureido}propionic acid methyl ester

HRID 852255노트

반응식

HRID 852255 반응식
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[NH2:20])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[O:22]=[C:23](Cl)OC(Cl)(Cl)Cl.[N-]=C=O.Cl.[CH3:34][O:35][C:36](=[O:57])[C@@H:37]([NH2:56])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([NH:45][C:46](=[O:55])[C:47]2[C:52]([Cl:53])=[CH:51][CH:50]=[CH:49][C:48]=2[Cl:54])=[CH:41][CH:40]=1.C(N(CC)CC)C>O1CCOCC1.ClCCl>[CH3:34][O:35][C:36](=[O:57])[C@@H:37]([NH:56][C:23]([NH:20][C:11]1[CH:12]=[C:13]([C:16]([F:17])([F:18])[F:19])[CH:14]=[CH:15][C:10]=1[S:7]([C:4]1[CH:3]=[CH:2][C:1]([CH3:21])=[CH:6][CH:5]=1)(=[O:9])=[O:8])=[O:22])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([NH:45][C:46](=[O:55])[C:47]2[C:48]([Cl:54])=[CH:49][CH:50]=[CH:51][C:52]=2[Cl:53])=[CH:41][CH:40]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 105034IsocyanateHCID 27681652-(4-Methylphenyl)sulfonyl-5-(trifluoromethyl)anilineHCID 23383932methyl (2S)-2-amino-3-{4-[(2,6-dichlorobenzoyl)amino]phenyl}propionate hydrochloride

생성물 1

HCID 69375653(S)-3-[4-(2,6-Dichlorobenzoylamino)phenyl]-2-{3-[2-(toluene-4-sulfonyl)-5-trifluoro methylphenyl]ureido}propionic acid methyl ester수율 163.9%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

반응 조건

온도
60 °C

실험 절차

A mixture of 2-(toluene-4-sulfonyl)-5-trifluoromethylphenylamine (0.2 g, 0.63 mmol) and diphosgene (0.061 g, 0.31 mmol) in dioxane (2 ml) was heated at 60° C. for 16 h. The solvent was removed under reduced pressure. The crude isocyanate was slowly added to a solution of (S)-2-amino-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester hydrochloride (0.25 g, 0.63 mmol) and triethylamine (0.063 g, 0.63 mmol) in dichloromethane (2 ml) and the resulting reaction mixture was stirred at room temperature overnight. The precipitate obtained was collected by filtration, washed several times with dichloromethane and dried under vacuum to yield the title compound (0.36 g, 82%) as a white solid.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting reaction mixture
  3. customThe precipitate obtained
  4. filtrationwas collected by filtration
  5. washwashed several times with dichloromethane
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-98bcc5831d584c3eab37773fb48e3440
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253171B2

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