HCID 9909570, compound → HCID 9886019, compound

HRID 617812Notes

Reaction equation

HRID 617812 reaction equation
Cl.[CH3:2][N:3]([CH3:29])[CH2:4][CH2:5][N:6]1[C:26](=[O:27])[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:15]4[C:16]5[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[C:17]=5[CH:18]=[CH:19][C:20]=4[N:8]([C:9]=23)[C:7]1=[O:28]>O.CO.Cl.[C].[Pd]>[CH3:2][N:3]([CH3:29])[CH2:4][CH2:5][N:6]1[C:26](=[O:27])[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:15]4[C:16]5[CH2:24][CH2:23][CH2:22][CH:21]([OH:25])[C:17]=5[CH:18]=[CH:19][C:20]=4[N:8]([C:9]=23)[C:7]1=[O:28]

Participants

6

Reactant 1

HCID 9909570HCID 9909570, compound

Product 1

HCID 9886019HCID 9886019, compoundYield 77.3%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

0.5 g (1.2 mmol) of the compound of Example 4 was dissolved in a mixture of water (50 ml) with methanol (25 ml) and 1.2 ml of 1 N hydrochloric acid was added thereto. Next, hydrogenation was effected in the presence of palladium-carbon under a hydrogen pressure of about 4.5 kg/cm2. After confirming the completion of the reaction by thin layer chromatography, the catalyst was filtered off and the residue was concentrated to about 2/3. After adding 50 ml of water and 5 ml of conc. aqueous ammonia thereto, the obtained mixture was extracted with ethyl acetate. The organic layer was taken up, washed with an aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography to thereby give 0.35 g of the title compound.

Workup

  1. additionwas added
  2. customthe completion of the reaction by thin layer chromatography
  3. filtrationthe catalyst was filtered off
  4. concentrationthe residue was concentrated to about 2/3
  5. additionAfter adding 50 ml of water and 5 ml of conc. aqueous ammonia
  6. extractionthe obtained mixture was extracted with ethyl acetate
  7. washwashed with an aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e40c7dabcb0c4dfeaa75c15d1c34dedf
Source dataset
uspto-grants-1999_09
Patent number
US05952335

Reaction notes

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