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

HRID 1060409Notes

Reaction equation

HRID 1060409 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-4c30f0a31a66443a8177ed3b90f92aa3
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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