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

HRID 852255ノート

反応式

HRID 852255 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-98bcc5831d584c3eab37773fb48e3440
出典データセット
uspto-grants-2007_08
特許番号
US07253171B2

反応ノート

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