HCID 68863530, compound → HCID 68865457, compound

HRID 1725970Notes

Reaction equation

HRID 1725970 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][C:16]([CH3:23])([CH3:22])[C:15](=O)[C:14]=2[C:13]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:10])=[O:9]>C(O)(=O)C.S(=O)(=O)(O)O.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][C:16]([CH3:22])([CH3:23])[CH2:15][C:14]=2[C:13]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:10])=[O:9]

Participants

5

Reactant 1

HCID 68863530HCID 68863530, compound

Product 1

HCID 68865457HCID 68865457, compoundYield 5.2%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

A mixture of Example 362D (600 mg) and Pd(OH)2 on carbon (370 mg) in 50 mL of acetic acid and 0.6 mL of concentrated sulfuric acid was reacted under 60 psi pressure for 5 days. After insoluble was filtered off and the filtrate was concentrated in vacuo, the residue was purified by silica gel column chromatography eluting with 10% ethyl acetate in n-hexane to provide 30 mg of the desired product. MS (ESI(+)) m/e 409 (M+NH4)+; MS (ESI(−)) m/e 390 (M−H)−.

Workup

  1. filtrationAfter insoluble was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe residue was purified by silica gel column chromatography
  4. washeluting with 10% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-5b761a393329448384a768866bd24369
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

Loading…