Methanol → N-(2,6-Dichlorobenzoyl)-4-[2-[N-(tert-butyl)sulfamoyl]phenyl]-L-phenylalanine

HRID 1060405Notes

Reaction equation

HRID 1060405 reaction equation
C[O:2][C:3](=[O:37])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29](=[O:36])(=[O:35])[NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14].[Li+].[OH-].CO>C1COCC1.O>[Cl:14][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([Cl:13])[C:7]=1[C:6]([NH:5][C@H:4]([C:3]([OH:37])=[O:2])[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29](=[O:36])(=[O:35])[NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:21][CH:22]=1)=[O:15]

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 53906758N-(2,6-Dichlorobenzoyl)-4-[2-[N-(tert-butyl)sulfamoyl]phenyl]-L-phenylalanine methyl ester

Product 1

HCID 54445287N-(2,6-Dichlorobenzoyl)-4-[2-[N-(tert-butyl)sulfamoyl]phenyl]-L-phenylalanineYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(2,6-Dichlorobenzoyl)-4-[2-[N-(tert-butyl)sulfamoyl]phenyl]-L-phenylalanine methyl ester (75 mg) was dissolved in THF (5 mL) and to this solution was added a solution of LiOH (monohydrate, 10 mg) in water (0.4 mL). Few drops of MeOH were added and the mixture was stirred at room temperature overnight. The mixture was evaporated, water was added to the residue and the mixture was acidified with 10% citric acid. The separated solid was collected by filtration, washed with water and dried to give 60 mg of the title compound. ESMS: m/z 549 (MH+), 547 ((M−H]−).

Workup

  1. customThe mixture was evaporated
  2. additionwater was added to the residue
  3. filtrationThe separated solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6cc257b89d1d480cb3a6cc7ce45ffc87
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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