Sulfuric Acid → HCID 54488538, compound

HRID 325792Notes

Reaction equation

HRID 325792 reaction equation
Cl.[C:2]([O:8][C:9]1[CH:47]=[CH:46][C:12]([C:13]([O:15][C:16]2[CH:17]=[C:18]([C:38](=[O:45])[CH2:39][NH:40][CH:41]3[CH2:44][CH2:43][CH2:42]3)[CH:19]=[C:20]([O:22][C:23](=[O:37])[C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:26][CH:25]=3)[CH:21]=2)=[O:14])=[CH:11][CH:10]=1)(=[O:7])[C:3]([CH3:6])([CH3:5])[CH3:4].[S:48](=O)(=[O:51])([OH:50])[OH:49]>C(O)C.[Pd]>[S:48]([O:45][CH:38]([C:18]1[CH:19]=[C:20]([O:22][C:23](=[O:37])[C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:26][CH:25]=2)[CH:21]=[C:16]([O:15][C:13](=[O:14])[C:12]2[CH:11]=[CH:10][C:9]([O:8][C:2](=[O:7])[C:3]([CH3:4])([CH3:5])[CH3:6])=[CH:47][CH:46]=2)[CH:17]=1)[CH2:39][NH:40][CH:41]1[CH2:44][CH2:43][CH2:42]1)([OH:51])(=[O:50])=[O:49]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 20464122HCID 20464122, compound

Product 1

HCID 54488538HCID 54488538, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 2.2 g of 3',5'-bis-(4-pivaloyloxybenzoyloxy)-2-cyclobutylamino acetophenone hydrochloride in 75 ml of ethanol was hydrogenated at 380 kPa (55 psig) and 45° C. for 18 hrs in the presence of 0.4 g 10% Pd/C. After filtering off the catalyst the filtrate was evaporated to dryness to give an oil as residue. This oil was partitioned between ethyl ether and 10% sodium carbonate solution. The ether phase was dried over MgSO4, filtered and evaporated to dryness to give a crystalline residue. The residue was dissolved in ethanol which was acidified with ethanolic sulphuric acid to pH 5.5. After evaporation, the residue was recrystallized from isopropanol/ethyl ether. The identity of the product was confirmed with NMR.

Workup

  1. filtrationAfter filtering off the catalyst the filtrate
  2. customwas evaporated to dryness
  3. customto give an oil as residue
  4. customThis oil was partitioned between ethyl ether and 10% sodium carbonate solution
  5. dry with materialThe ether phase was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customto give a crystalline residue
  9. customAfter evaporation
  10. customthe residue was recrystallized from isopropanol/ethyl ether

Sources & evidence

ORD record
ord-94e7053e907947e5b494ba93d3b38eb3
Source dataset
uspto-grants-1984_04
Patent number
US04442300

Reaction notes

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