Bromotrimethylsilane → HCID 54549438, compound

HRID 476705Notes

Reaction equation

HRID 476705 reaction equation
C[O:2][P:3]([CH2:23][NH:24][C:25]([C@@H:27]([NH:32][C:33]([C@@H:35]1[CH2:39][CH2:38][CH2:37][N:36]1[C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41])=[O:34])[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:26])([CH2:5][CH:6]([C:11](=[O:22])[NH:12][C@H:13]([C:18](=[O:21])[NH:19][CH3:20])[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4].Br[Si](C)(C)C>ClCCl>[CH2:43]([O:42][C:40]([N:36]1[CH2:37][CH2:38][CH2:39][C@H:35]1[C:33]([NH:32][C@H:27]([C:25]([NH:24][CH2:23][P:3]([CH2:5][CH:6]([C:11](=[O:22])[NH:12][C@H:13]([C:18](=[O:21])[NH:19][CH3:20])[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:7][CH:8]([CH3:9])[CH3:10])(=[O:2])[OH:4])=[O:26])[CH2:28][CH:29]([CH3:30])[CH3:31])=[O:34])=[O:41])[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 67863547HCID 67863547, compound

Product 1

HCID 54549438HCID 54549438, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.11 g of benzyl(S)-2-[[(S)-1-[[[methoxy[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinyl]methyl]carbamoyl]-3-methylbutyl]carbamoyl]-1-pyrrolidinecarboxylate was dissolved in 4 ml of dichloromethane and 0.5 ml of bromotrimethylsilane was added. The mixture was stirred at room temperature for 1.5 hours and the solvent was removed by evaporation. The residue was dissolved in 5 ml of acetone and there were then added 1 ml of water and 0.5 g of sodium hydrogen carbonate followed by 50 mg of benzyl chloroformate. After stirring at room temperature for 2.5 hours, the solvent was removed by evaporation. The residue was dissolved in 15 ml of 1M sodium hydroxide solution and the resulting solution was extracted three times with 15 ml of diethyl ether each time. The aqueous solution was acidified with 10% sulfuric acid, saturated with sodium chloride solution and extracted five times with 20 ml of 5% methanol in dichloromethane each time. The organic extracts were dried over anhydrous sodium sulfate and evaporated to give 0.1 g of [[[N-[1-[(benzyloxy)carbonyl]-L-prolyl]-L-leucyl]amino]methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid in the form of a white foam.

Workup

  1. customthe solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in 5 ml of acetone
  3. additionthere were then added 1 ml of water and 0.5 g of sodium hydrogen carbonate
  4. stirringAfter stirring at room temperature for 2.5 hours
  5. customthe solvent was removed by evaporation
  6. dissolutionThe residue was dissolved in 15 ml of 1M sodium hydroxide solution
  7. extractionthe resulting solution was extracted three times with 15 ml of diethyl ether each time
  8. extractionextracted five times with 20 ml of 5% methanol in dichloromethane each time
  9. dry with materialThe organic extracts were dried over anhydrous sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-fe33381813634f789d79f69d22ddf9b3
Source dataset
uspto-grants-1989_12
Patent number
US04885283

Reaction notes

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