Trifluoroacetic acid → [(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl][(2-phenylmaleimido)methyl]phosphinic acid

HRID 476699Notes

Reaction equation

HRID 476699 reaction equation
C[O:2][P:3]([CH2:19][CH:20]([C:25](=[O:36])[NH:26][C@H:27]([C:32](=[O:35])[NH:33][CH3:34])[CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:21][CH:22]([CH3:24])[CH3:23])([CH2:5][N:6]1[C:10](=[O:11])[CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]1=[O:18])=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:23][CH:22]([CH3:24])[CH2:21][CH:20]([C:25](=[O:36])[NH:26][C@H:27]([C:32](=[O:35])[NH:33][CH3:34])[CH2:28][CH:29]([CH3:30])[CH3:31])[CH2:19][P:3]([CH2:5][N:6]1[C:10](=[O:11])[CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]1=[O:18])(=[O:2])[OH:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54173205HCID 54173205, compound

Product 1

HCID 18636025[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl][(2-phenylmaleimido)methyl]phosphinic acidYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.1 g of [(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl][(2-phenylmaleimido)methyl]phosphinic acid methyl ester was dissolved in 1 ml of dichloromethane and 2 ml of trifluoroacetic acid were added. The mixture was stirred at room temperature for 2 hours and the solvent was then removed by evaporation. The residue was taken up in 30 ml of acetone/dichloromethane (1:1) and the solution was evaporated to give 95 mg of [(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl][(2-phenylmaleimido)methyl]phosphinic acid in the form of a tan colored foam.

Workup

  1. customthe solvent was then removed by evaporation
  2. customthe solution was evaporated

Sources & evidence

ORD record
ord-719f906e8c834727a74c7186fd084633
Source dataset
uspto-grants-1989_12
Patent number
US04885283

Reaction notes

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