Trifluoroacetic acid → [(2,5-dioxo-1-imidazolidinyl)methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid

HRID 476723Notes

Reaction equation

HRID 476723 reaction equation
C([O:3][P:4]([CH2:24][N:25]1[C:29](=[O:30])[CH2:28][NH:27][C:26]1=[O:31])([CH2:6][CH:7]([C:12](=[O:23])[NH:13][C@H:14]([C:19](=[O:22])[NH:20][CH3:21])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:5])C.Br[Si](C)(C)C.FC(F)(F)C(O)=O>ClCCl>[O:31]=[C:26]1[NH:27][CH2:28][C:29](=[O:30])[N:25]1[CH2:24][P:4]([CH2:6][CH:7]([C:12](=[O:23])[NH:13][C@H:14]([C:19](=[O:22])[NH:20][CH3:21])[CH2:15][CH:16]([CH3:17])[CH3:18])[CH2:8][CH:9]([CH3:11])[CH3:10])(=[O:3])[OH:5]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 76113BromotrimethylsilaneHCID 67864219[(2,5-dioxo-1-imidazolidinyl)methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester

Product 1

HCID 67863568[(2,5-dioxo-1-imidazolidinyl)methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acidYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

60 mg (0.13 mmol) of [(2,5-dioxo-1-imidazolidinyl)methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester were dissolved in 1 ml of dichloromethane and the solution was stirred at room temperature for 3 hours in the presence of 1 ml of bromotrimethylsilane and 0.1 ml of trifluoroacetic acid. The solvent was removed by evaporation. The residue was treated three times with acetone/water (9:1) and the solvent was removed by evaporation each time. Finally, the product was triturated with diethyl ether to yield 55 mg of [(2,5-dioxo-1-imidazolidinyl)methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid in the form of a foam.

Workup

  1. customThe solvent was removed by evaporation
  2. additionThe residue was treated three times with acetone/water (9:1)
  3. customthe solvent was removed by evaporation each time
  4. customFinally, the product was triturated with diethyl ether

Sources & evidence

ORD record
ord-8762f5d9ad314140a2cfe8e5df1aae45
Source dataset
uspto-grants-1989_12
Patent number
US04885283

Reaction notes

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