Methanesulfonyl chloride → N-[2-chloro-4-(N,N-dimethanesulfonylamino)benzoyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

HRID 24653Notes

Reaction equation

HRID 24653 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8](=[O:36])[C@H:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH3:35])=[CH:24][CH:23]=1)[NH:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=1[Cl:19].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:6][O:7][C:8](=[O:36])[C@H:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH3:35])=[CH:24][CH:23]=1)[NH:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([N:18]([S:2]([CH3:1])(=[O:4])=[O:3])[S:2]([CH3:1])(=[O:4])=[O:3])=[CH:14][C:13]=1[Cl:19]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 54392214N-(4-amino-2-chlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

Product 1

HCID 53775032N-[2-chloro-4-(N,N-dimethanesulfonylamino)benzoyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

MeSO2Cl (24 μL) was added to a solution of N-(4-amino-2-chlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (56.0 mg) in anhydrous CH2Cl2 (1 mL) containing DIEA (66.6 μL). The resulting mixture was stirred at room temperature under N2 for 3 h and diluted with CH2Cl2, washed with 1N HCl, water, dried (MgSO4) and evaporated. The residue was purified through a silica gel column using CH2Cl2 as an eluent to give N-[2-chloro-4-(N,N-dimethanesulfonylamino)benzoyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (59.4 mg). ESMS: m/z 595 (MH+).

Workup

  1. washwashed with 1N HCl, water
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified through a silica gel column

Sources & evidence

ORD record
ord-009ee9839d024765a4afd8b86e29663a
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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