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

HRID 1670504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1670504
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].[NH2:22][CH2:23][CH:24]([NH:51][C:52](=[O:61])[O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:25](=[O:50])[NH:26][CH:27]([C:36](=[O:49])[N:37]([CH2:41][CH:42]([O:46][CH2:47][CH3:48])[O:43][CH2:44][CH3:45])[CH:38]([CH3:40])[CH3:39])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1>C(Cl)Cl>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][CH:27]([NH:26][C:25]([CH:24]([NH:51][C:52](=[O:61])[O:53][CH2:54][C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH2:23][NH:22][S:18]([C:12]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=2[Cl:10])(=[O:20])=[O:19])=[O:50])[C:36](=[O:49])[N:37]([CH2:41][CH:42]([O:43][CH2:44][CH3:45])[O:46][CH2:47][CH3:48])[CH:38]([CH3:40])[CH3:39])=[CH:34][CH:33]=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-37b186448a8243b8955a2d65b2e49bea
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994168B2

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