Hydrochloric Acid → HCID 18770702, compound

HRID 479482Notes

Reaction equation

HRID 479482 reaction equation
[CH3:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][CH:9]([NH:11]C(=O)OCC2C=CC=CC=2)[CH3:10])=[O:7])=[CH:4][CH:3]=1.[ClH:24].[H][H]>CO.[Pd]>[ClH:24].[NH2:11][CH:9]([NH:8][C:6](=[O:7])[C:5]1[CH:22]=[CH:23][C:2]([CH3:1])=[CH:3][CH:4]=1)[CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 18770653HCID 18770653, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18770702HCID 18770702, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of Example 29B (66 mg, 0.21 mmol) in methanol (9 mL) at ambient temperature was treated with 10% Pd/C (20 mg) aid sufficient 1M HCl to solubilize the substrate (ca. 0.20 mL). The system was equipped with a hydrogen balloon and stirred for 4 hours at ambient temperature. The reaction mixture was purged with nitrogen, filtered through diatomaceous earth (Celite®), rinsed with methanol and water, and the aqueous filtrate was washed with diethyl ether (2×15 mL). The aqueous layer was lyophilized providing 38 mg of the desired product as a white solid.

Workup

  1. customThe reaction mixture was purged with nitrogen
  2. filtrationfiltered through diatomaceous earth (Celite®)
  3. washrinsed with methanol and water
  4. washthe aqueous filtrate was washed with diethyl ether (2×15 mL)

Sources & evidence

ORD record
ord-592747491f0e433594b0fdedb8f66440
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

Loading…