Hydrochloric Acid → HCID 69710452, compound

HRID 2121915Notes

Reaction equation

HRID 2121915 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[O:23][C:9]2=[CH:10][CH:11]=[C:12]3[C:16]([N:15]([CH2:17][C@@H:18]([N:20]=[N+]=[N-])[CH3:19])[N:14]=[CH:13]3)=[C:8]2[CH2:7]1)=[O:5])[CH3:2].Cl>CO.C(O)C.[Pd]>[CH2:1]([O:3][C:4]([CH:6]1[O:23][C:9]2=[CH:10][CH:11]=[C:12]3[C:16]([N:15]([CH2:17][C@@H:18]([NH2:20])[CH3:19])[N:14]=[CH:13]3)=[C:8]2[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 131724356HCID 131724356, compound

Product 1

HCID 69710452HCID 69710452, compoundYield 25.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of the product from Step A (0.13 g, 0.41 mmol) in methanol (20 mL) was added palladium-on-carbon (10%, 0.015 g). This mixture was stirred overnight under an atmosphere of hydrogen (0.4 mL of a 2 N HCl in ethanol was added to protect the ethyl ester). The reaction mixture was filtered and purified by reversed phase HPLC (gradient of acetonitrile in water, 0% to 50% with 0.1% trifluoroacetic acid). The desired fractions were combined, concentrated, treated with 2 N HCl in ethanol (10 mL) and evaporated to a residue which was dried under high vacuum at 78° C. overnight to afford an amorphous solid (0.03 g, 20%): LC/MS (+APCI) m/z 290 (M+H).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. custompurified by reversed phase HPLC (gradient of acetonitrile in water, 0% to 50% with 0.1% trifluoroacetic acid)
  4. concentrationconcentrated
  5. additiontreated with 2 N HCl in ethanol (10 mL)
  6. customevaporated to a residue which
  7. customwas dried under high vacuum at 78° C. overnight

Sources & evidence

ORD record
ord-014e9d48f59f48e48862e7aa81d3a1b8
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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