Diisopropylethylamine → Methyl 2-benzyloxycarbonylamino-3-(2,4-dichlorobenzenesulfonylamino)-2-methylpropionate

HRID 1994433ノート

反応式

HRID 1994433 の反応式
[NH2:1][CH2:2][C:3]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[S:28](Cl)(=[O:30])=[O:29].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:13]([O:12][C:10]([NH:9][C:3]([CH3:8])([CH2:2][NH:1][S:28]([C:22]1[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=1[Cl:20])(=[O:30])=[O:29])[C:4]([O:6][CH3:7])=[O:5])=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 68692239Methyl 3-amino-2-benzyloxycarbonylamino-2-methylpropionate

生成物 1

HCID 68695213Methyl 2-benzyloxycarbonylamino-3-(2,4-dichlorobenzenesulfonylamino)-2-methylpropionate収率 50%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

0.103 g (0.341 mmol) of methyl 3-amino-2-benzyloxycarbonylamino-2-methylpropionate, 0.109 g (0.443 mmol) of 2,4 dichlorobenzenesulfonyl chloride and 0.237 ml (1.36 mmol) of DIEA are dissolved in 2 ml of DCM. The mixture is stirred at room temperature overnight. 2 ml are added to the reaction solution, and then the organic phase is separated off and dried over MgSO4, and the solvent is removed in vacuo. The crude product is purified by chromatography on 4 g of SiO2, EtOAc/DCM as eluent (gradient of 0-40%). 0.081 g of the desired product is obtained as an oil. MW=474 (calculated, monoisotopic), measured value: (M+H)+ 475.

後処理

  1. addition2 ml are added to the reaction solution
  2. customthe organic phase is separated off
  3. dry with materialdried over MgSO4
  4. customthe solvent is removed in vacuo
  5. customThe crude product is purified by chromatography on 4 g of SiO2, EtOAc/DCM as eluent (gradient of 0-40%)

出典と根拠

ORDレコード
ord-4500bed916d742f5bc26b5619108e056
出典データセット
uspto-grants-2010_01
特許番号
US07652007B2

反応ノート

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