Hydrochloric Acid → HCID 70055746, compound

HRID 1977981Notes

Reaction equation

HRID 1977981 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([C:16]#[C:17][CH2:18][N:19]2[CH2:24][CH2:23][C:22]3([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:21][CH2:20]2)[CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[OH-].[Na+].CO>C(OCC)(=O)C.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[ClH:3].[Cl:3][C:4]1[CH:5]=[C:6](/[CH:16]=[CH:17]\[CH2:18][N:19]2[CH2:20][CH2:21][C:22]3([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:23][CH2:24]2)[CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 21996598HCID 21996598, compound

Product 1

HCID 70055746HCID 70055746, compound

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3 g of the hydrochloride of the acetylenic compound obtained in Example 1 above are liberated by aqueous 10% sodium hydroxide solution. The oil obtained after extraction with diethyl ether is washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated under vacuum. The residue thus obtained is taken up in 100 ml of ethyl acetate, 5 ml of methanol are added, followed by 0.2 g of Pd/BaSO4 and the reaction mixture is hydrogenated at room temperature and at atmospheric pressure. The catalyst is separated out by filtration through silica, the filtrate is concentrated under vacuum and the residual oil is then chromatographed on a column of silica gel, eluent: 98/2 (v/v) dichloromethane/methanol. Concentration of the pure fractions gives the hydrochloride, which is recrystallized from ethyl acetate; Y=44%; m.p.=238° C.

Workup

  1. customThe oil obtained
  2. extractionafter extraction with diethyl ether
  3. washis washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under vacuum
  6. customThe residue thus obtained
  7. customis hydrogenated at room temperature and at atmospheric pressure
  8. customThe catalyst is separated out by filtration through silica
  9. concentrationthe filtrate is concentrated under vacuum
  10. customthe residual oil is then chromatographed on a column of silica gel, eluent

Sources & evidence

ORD record
ord-046b3f9fbc824424841f472fa9981cee
Source dataset
uspto-grants-2001_05
Patent number
US06235791B1

Reaction notes

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