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

HRID 852255Notes

Reaction equation

HRID 852255 reaction equation
[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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-98bcc5831d584c3eab37773fb48e3440
Source dataset
uspto-grants-2007_08
Patent number
US07253171B2

Reaction notes

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