Bromotrimethylsilane → HCID 67864225, compound

HRID 2073270Notes

Reaction equation

HRID 2073270 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:15][C@H:14]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:13][C@H:12]2/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][P:32]([O:37]CC)([O:34]CC)=[O:33])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[Si](C)(C)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:15][C@H:14]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:13][C@H:12]2/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][P:32]([OH:37])([OH:34])=[O:33])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86743851HCID 86743851, compound

Product 1

HCID 67864225HCID 67864225, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-1-(4-chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-diethoxyphosphoryl-1-pentenyl]pyrrolidine (146 mg) in dichloromethane (5.0 ml) was added bromotrimethylsilane (0.1 ml) and the mixture was stirred at room temperature for 3 hours. After the mixture was evaporated to dryness, the residue was dissolved in acetone (5 ml), and water (20 μl) was added thereto. The mixture was stirred at room temperature for 1 hour and the solvent was evaporated in vacuo. The residue was solidified with a mixture of chloroform and water to give (2S,4R)-1-(4-chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-phosphono-1-pentenyl]pyrrolidine (70 mg) as a powder.

Workup

  1. customAfter the mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in acetone (5 ml)
  3. additionwater (20 μl) was added
  4. stirringThe mixture was stirred at room temperature for 1 hour
  5. customthe solvent was evaporated in vacuo
  6. additionThe residue was solidified with a mixture of chloroform and water

Sources & evidence

ORD record
ord-1bcb09cbca514cb6bcf11966ea814e98
Source dataset
uspto-grants-1990_04
Patent number
US04916152

Reaction notes

Loading…