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

HRID 476697
Notes
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Reaction equation

HRID 476697 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 67864256[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl](succinimidomethyl)phosphinic acid methyl ester

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 each time. The residue was dissolved in 5 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 each time
  3. dissolutionThe residue was dissolved in 5 ml of acetone
  4. waitAfter standing at room temperature for 15 minutes
  5. customthe solvent was removed by evaporation
  6. dissolutionthe residue was dissolved in 20 ml of acetone/dichloromethane (1:2)
  7. customThe solution was then evaporated

Sources & evidence

ORD record
ord-a9bef729678546a68d5932bfd0735bd4
Source dataset
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04885283

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes