Sulfuric Acid → HCID 11402700, compound

HRID 1927577Notes

Reaction equation

HRID 1927577 reaction equation
OS(O)(=O)=O.[CH3:6][C:7]1[O:11][C:10]([C@H:12]([NH:15][C@H:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:17][O:18][Si](C)(C)C)[CH2:13][CH3:14])=[CH:9][CH:8]=1.[NH4+].[OH-].[OH-].[Na+]>CC(OC)(C)C.O.C(O)(CC)C>[CH3:6][C:7]1[O:11][C:10]([C@H:12]([NH:15][C@H:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:17][OH:18])[CH2:13][CH3:14])=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 11461702HCID 11461702, compound

Product 1

HCID 11402700HCID 11402700, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6568(+-)-2-ButanolSolventHCID 15413tert-Butyl methyl etherSolvent2×

Procedure

700 ml of 5M H2SO4 are cooled to 5° and 232 g of [(R)-1-(5-Methyl-furan-2-yl)-propyl]-((R)-1-phenyl-2-trimethylsilanyloxy-ethyl)-amine dissolved in 1 l of TBME are added dropwise over a period of 30 minutes at 5-10°. 345 ml of sec-BuOH and 345 ml of H2O are added and the reaction mixture obtained is slowly warmed to rt. The aqueous layer obtained is separated. The organic portion obtained is adjusted to pH 11 with 2.5M NH4OH, the aqueous layer is separated and the organic phases obtained are washed 2× with brine. The aqueous layer obtained are back-extracted with 1 l of EtOAc, the organic portions obtained are combined, dried over Na2SO4, filtered and solvent is evaporated. A residue obtained is dissolved in 500 ml of TBME and 500 ml of H2O and the pH is adjusted to pH 11 with 2.5M NaOH and extracted 2× with 6 l of TBME. The organic portion obtained is dried, filtered and solvent is evaporated. The title compound is obtained.

Workup

  1. additionare added dropwise over a period of 30 minutes at 5-10°
  2. customthe reaction mixture obtained
  3. customThe aqueous layer obtained
  4. customis separated
  5. customThe organic portion obtained
  6. customthe aqueous layer is separated
  7. customthe organic phases obtained
  8. washare washed 2× with brine
  9. customThe aqueous layer obtained
  10. extractionare back-extracted with 1 l of EtOAc
  11. customthe organic portions obtained
  12. dry with materialdried over Na2SO4
  13. filtrationfiltered
  14. customsolvent is evaporated
  15. customA residue obtained
  16. extractionextracted 2× with 6 l of TBME
  17. customThe organic portion obtained
  18. customis dried
  19. filtrationfiltered
  20. customsolvent is evaporated

Sources & evidence

ORD record
ord-03e3475f51ce463b9ef80a02fe02c9ae
Source dataset
uspto-grants-2012_05
Patent number
US08183281B2

Reaction notes

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