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

HRID 1994433Notes

Reaction equation

HRID 1994433 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-4500bed916d742f5bc26b5619108e056
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

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