HCID 54239494, compound → HCID 54116286, compound

HRID 2418272Notes

Reaction equation

HRID 2418272 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([CH3:32])[CH2:23][N:24]3[CH2:29][C@H:28]([CH3:30])[O:27][C@H:26]([CH3:31])[CH2:25]3)=[CH:17][CH:16]=2)(O)[CH3:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.OS(O)(=O)=O.[Pd]>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([CH3:32])[CH2:23][N:24]3[CH2:25][C@H:26]([CH3:31])[O:27][C@H:28]([CH3:30])[CH2:29]3)=[CH:17][CH:16]=2)[CH3:13])=[CH:9][CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 1

HCID 54239494HCID 54239494, compound

Product 1

HCID 54116286HCID 54116286, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 50 g of (VII) in 1 l of glacial acetic acid and 30 ml of concentrated H2SO4 was hydrogenated in the presence of 5 g of 5% strength Pd/C at room temperature and under 5 bar, until the pressure remained constant. The catalyst was filtered off and the filtrate was made alkaline with dilute aqueous NaOH. The crude product was extracted with CH2Cl, and the solution was washed with H2O, dried over Na2SO4 and concentrated. Distillation of the residue gave 40 g of product of boiling point 200°-202° C./0.3 mbar.

Workup

  1. filtrationThe catalyst was filtered off
  2. extractionThe crude product was extracted with CH2Cl
  3. washthe solution was washed with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. distillationDistillation of the residue

Sources & evidence

ORD record
ord-a971f5c12a2c48c5811a1b7734a7886f
Source dataset
uspto-grants-1984_09
Patent number
US04472412

Reaction notes

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