Triethylamine → N-(2,6-dichlorobenzoyl)-4-[2-(methanesulfonylamino)phenyl]-L-phenylalanine methyl ester

HRID 24637Notes

Reaction equation

HRID 24637 reaction equation
OC(C(F)(F)F)=O.[CH3:8][O:9][C:10](=[O:37])[C@H:11]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH2:36])=[CH:26][CH:25]=1)[NH:12][C:13](=[O:22])[C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21].CCN(CC)CC.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>C(Cl)Cl.O>[CH3:8][O:9][C:10](=[O:37])[C@H:11]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH:36][S:46]([CH3:45])(=[O:48])=[O:47])=[CH:26][CH:25]=1)[NH:12][C:13](=[O:22])[C:14]1[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131723775N-(2,6-dichlorobenzoyl)-4-(2-aminophenyl)-L-phenylalanine methyl ester TFA salt

Product 1

HCID 54025320N-(2,6-dichlorobenzoyl)-4-[2-(methanesulfonylamino)phenyl]-L-phenylalanine methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

N-(2,6-Dichlorobenzoyl)-4-(2-aminophenyl)-L-phenylalanine methyl ester TFA salt (90 mg) was dissolved in dry CH2Cl2 (5 mL). To this solution was added Et3N (85 μL) and MsCl (30 μL). The mixture was stirred at room temperature for 3 h and diluted with water. The organic phase was dried (MgSO4) and evaporated to give N-(2,6-dichlorobenzoyl)-4-[2-(methanesulfonylamino)phenyl]-L-phenylalanine methyl ester.

Workup

  1. dry with materialThe organic phase was dried (MgSO4)
  2. customevaporated

Sources & evidence

ORD record
ord-0c9d4db4b39d4b469e3818482a703122
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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