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

HRID 1670504ノート

反応式

HRID 1670504 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 86761389Benzyl (2-(2,4-dichlorobenzenesulfonylamino)-1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethylcarbamoyl}ethyl)carbamate収率 63.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-37b186448a8243b8955a2d65b2e49bea
出典データセット
uspto-grants-2011_08
特許番号
US07994168B2

反応ノート

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