Water → HCID 53677101, compound

HRID 728886Notes

Reaction equation

HRID 728886 reaction equation
C[Si](Br)(C)C.C(OC([NH:13][C@H:14]([CH:18]=[C:19]([CH3:27])[CH2:20][P:21]([O:25]C)([O:23]C)=[O:22])[C:15]([OH:17])=[O:16])=O)(C)(C)C.O>ClCCl>[NH2:13][C@H:14]([CH:18]=[C:19]([CH3:27])[CH2:20][P:21]([OH:25])([OH:23])=[O:22])[C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 76113BromotrimethylsilaneHCID 57025855HCID 57025855, compound

Product 1

HCID 53677101HCID 53677101, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.71 ml of trimethylsilyl bromide is added at 0° to a solution of 123 mg of 9 in 3 ml of dichloromethane. After stirring at 0° for 4 hours, 20 ml of water are added. After 30 minutes, the dichloromethane phase is separated off and washed three times with 15 ml of water each time. The aqueous phases are extracted three times with 20 ml of dichloromethane each time and concentrated by evaporation in vacuo. The residue is dissolved in 10 ml of 5N hydrochloric acid and is then stirred for 48 hours, diluted with 20 ml of water and extracted three times with 20 ml of dichloromethane each time. The aqueous phase is concentrated by evaporation in vacuo, and the residue is dried under a high vacuum and dissolved in 3 ml of etharol, and then approximately 1 ml of propylene oxide is added dropwise thereto. The suspension is filtered. Washing of the filtration residue with ethanol and drying under a high vacuum at roomtemperature yields 62 mg of 10, m.p. 165° C. (decomposition).

Workup

  1. waitAfter 30 minutes
  2. customthe dichloromethane phase is separated off
  3. washwashed three times with 15 ml of water each time
  4. extractionThe aqueous phases are extracted three times with 20 ml of dichloromethane each time
  5. concentrationconcentrated by evaporation in vacuo
  6. dissolutionThe residue is dissolved in 10 ml of 5N hydrochloric acid
  7. stirringis then stirred for 48 hours
  8. additiondiluted with 20 ml of water
  9. extractionextracted three times with 20 ml of dichloromethane each time
  10. concentrationThe aqueous phase is concentrated by evaporation in vacuo
  11. customthe residue is dried under a high vacuum
  12. dissolutiondissolved in 3 ml of etharol
  13. additionapproximately 1 ml of propylene oxide is added dropwise
  14. filtrationThe suspension is filtered
  15. washWashing of the filtration residue with ethanol
  16. customdrying under a high vacuum at roomtemperature

Sources & evidence

ORD record
ord-1ce97afe9dd54b31bfb9252a824ab791
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

Loading…