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

HRID 1994433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1994433
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-4500bed916d742f5bc26b5619108e056
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652007B2

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