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

HRID 1670504노트

반응식

HRID 1670504 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-37b186448a8243b8955a2d65b2e49bea
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994168B2

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