Hydrochloric Acid → HCID 44482146, compound

HRID 2094692Notes

Reaction equation

HRID 2094692 reaction equation
O[CH:2]([C:12]1[CH:13]=[C:14]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:15]([NH:17][C:18]1([C:27]([OH:29])=[O:28])[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1)=[O:16])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1.Cl.[H][H]>C(O)C.CO.[Pd]>[CH3:34][O:33][C:32]1[CH:31]=[CH:30][C:14]([C:15]([NH:17][C:18]2([C:27]([OH:29])=[O:28])[CH2:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:26]2)=[O:16])=[CH:13][C:12]=1[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 67076255HCID 67076255, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44482146HCID 44482146, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

The compound of example 114 (20 mg, 0.043 mmol) was dissolved in ethanol (2 ml), a 0.5 M solution of hydrogen chloride in methanol (0.2 ml) was added and the mixture was hydrogenated overnight in the presence of palladium on charcoal (10%) at room temperature at a hydrogen pressure of 5 bar (complete conversion of the starting compound). After filtration over a small plug of silica gel and evaporation, the residue was purified by preparative RP HPLC (water/ACN gradient).

Workup

  1. filtrationAfter filtration
  2. customover a small plug of silica gel and evaporation
  3. customthe residue was purified by preparative RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-e06ac2a7ae7a4a1985c836d19ef3f530
Source dataset
uspto-grants-2013_05
Patent number
US08445530B2

Reaction notes

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