Diisopropylethylamine → Benzyl (2-(2,4-dichlorobenzenesulfonylamino)-1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethylcarbamoyl}ethyl)carbamate

HRID 1994405Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1994405
CCN(C(C)C)C(C)C.[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[S:18](Cl)(=[O:20])=[O:19].[CH2:22]([O:29][C:30](=[O:61])[NH:31][CH:32]([C:35](=[O:60])[NH:36][CH:37]([C:46](=[O:59])[N:47]([CH2:51][CH:52]([O:56][CH2:57][CH3:58])[O:53][CH2:54][CH3:55])[CH:48]([CH3:50])[CH3:49])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1)[CH2:33][NH2:34])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([O:29][C:30](=[O:61])[NH:31][CH:32]([C:35](=[O:60])[NH:36][CH:37]([C:46](=[O:59])[N:47]([CH2:51][CH:52]([O:53][CH2:54][CH3:55])[O:56][CH2:57][CH3:58])[CH:48]([CH3:50])[CH3:49])[CH2:38][C:39]1[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=1)[CH2:33][NH:34][S:18]([C:12]1[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=1[Cl:10])(=[O:20])=[O:19])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 86761390Benzyl (2-amino-1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethylcarbamoyl}ethyl)carbamate

Produkt 1

HCID 86761389Benzyl (2-(2,4-dichlorobenzenesulfonylamino)-1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethylcarbamoyl}ethyl)carbamateAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.94 ml (11.09 mmol) of DIEA and 1.5 g (6.1 mmol) of 2,4-dichlorophenylsulfonyl chloride are added to a solution of 3.2 g (5.54 mmol) of benzyl(2-amino-1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethylcarbamoyl}ethyl)carbamate in 75 ml of DCM. The solution is stirred at room temperature overnight. The solution is then concentrated in vacuo, and the residue is purified by column chromatography on 100 g of SiO2 (eluent DCM followed by 20% EtOAc/DCM). 2.78 g of the desired product are obtained as a colorless foam. MW=784.19 (calculated, monoisotopic); measured value (M+Na)+=807.24

Aufarbeitung

  1. concentrationThe solution is then concentrated in vacuo
  2. customthe residue is purified by column chromatography on 100 g of SiO2 (eluent DCM followed by 20% EtOAc/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-b30d6ccdbb394d4784633c1cf468db63
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652007B2

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