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

HRID 476718Notes

Reaction equation

HRID 476718 reaction equation
C([O:3][P:4]([CH2:24][N:25]1[C:30](=[O:31])[CH2:29][CH2:28][CH2:27][C:26]1=[O:32])([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>ClCCl>[C:26]1(=[O:32])[N:25]([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]([CH3:18])[CH3:17])[CH2:8][CH:9]([CH3:11])[CH3:10])(=[O:3])[OH:5])[C:30](=[O:31])[CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 53732201(glutarimidomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester

Product 1

HCID 18636022(glutarimidomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acidYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.11 g (0.23 mmol) of (glutarimidomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester was dissolved in 4 ml of dicloromethane and the solution was stirred overnight in the presence of 2 ml of bromotrimethylsilane. The solvent was removed by evaporation and the residue was dissolved in 5 ml of acetone/water (9:1). The solvent was removed by evaporation and this treatment was repeated once more to give 0.1 g of (glutarimidomethyl)[(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. dissolutionthe residue was dissolved in 5 ml of acetone/water (9:1)
  3. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-5eaf1d614af8460e8f57de93b68bbaa9
Source dataset
uspto-grants-1989_12
Patent number
US04885283

Reaction notes

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