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

HRID 1084991Notes

Reaction equation

HRID 1084991 reaction equation
C[O:2][P:3]([CH2:13][CH:14]([C:19](=[O:30])[NH:20][C@H:21]([C:26](=[O:29])[NH:27][CH3:28])[CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:15][CH:16]([CH3:18])[CH3:17])([CH2:5][N:6]1[C:10](=[O:11])[CH2:9][CH2:8][C:7]1=[O:12])=[O:4].Br[Si](C)(C)C>ClCCl>[CH3:17][CH:16]([CH3:18])[CH2:15][CH:14]([C:19](=[O:30])[NH:20][C@H:21]([C:26](=[O:29])[NH:27][CH3:28])[CH2:22][CH:23]([CH3:24])[CH3:25])[CH2:13][P:3]([CH2:5][N:6]1[C:10](=[O:11])[CH2:9][CH2:8][C:7]1=[O:12])(=[O:2])[OH:4]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 67864256HCID 67864256, compound

Product 1

HCID 18636028[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl](succinimidomethyl)phosphinic acidYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

60 mg of [(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl](succinimidomethyl)phosphinic acid methyl ester were dissolved in 5 ml of dichloromethane, 0.5 ml of bromotrimethylsilane was added and the mixture was stirred at room temperature for 1.5 hours. The solvent was removed by evaporation and the residue was then re-evaporated twice with 20 ml of acetone and 0.25 ml of water. After standing at room temperature for 15 minutes, the solvent was removed by evaporation and the residue was dissolved in 20 ml of acetone/dichloromethane (1:2). The solution was then evaporated to give 56 mg of [(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl](succinimidomethyl)phosphinic acid in the form of a white foam.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was then re-evaporated twice with 20 ml of acetone and 0.25 ml of water
  3. waitAfter standing at room temperature for 15 minutes
  4. customthe solvent was removed by evaporation
  5. dissolutionthe residue was dissolved in 20 ml of acetone/dichloromethane (1:2)
  6. customThe solution was then evaporated

Sources & evidence

ORD record
ord-31fb3c3f11fd4bff88652ba836fc4c05
Source dataset
uspto-grants-1991_04
Patent number
US05006651

Reaction notes

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