HCID 66999834, compound → HCID 67000009, compound

HRID 560187Notes

Reaction equation

HRID 560187 reaction equation
C(OC(NCCC[N:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24](=[O:32])[NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:21][CH:22]=2)[CH:17]=[C:16]1[C:33]([OH:35])=[O:34])=O)C1C=CC=CC=1>CO.[Pd]>[C:33]([OH:35])(=[O:34])[CH3:16].[NH2:15][CH2:16][CH2:17][CH2:18][C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[C:20]([C:24](=[O:32])[NH:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:19]=2)[NH:15][C:16]=1[C:33]([OH:35])=[O:34]

Participants

4

Reactant 1

HCID 66999834HCID 66999834, compound

Product 1

HCID 67000009HCID 67000009, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A reaction flask equipped with a stir bar was charged with a solution of the above carboxylic acid (40 mg, 0.08 mmol) in methanol (10 mL). 10% Palladium on carbon (20 mg) was added. The reaction mixture was sealed with a rubber septum and the air was evacuated under house vacuum. A balloon filled with hydrogen gas was attached to the flask, and the reaction mixture was stirred for 5 h. The mixture was filtered through diatomaceous earth and the filtrate was evaporated. The residue was washed with 2 mL of ether and 2 mL of hexane. The product was dried and 5 mL of acetic acid was added. The acetic acid was evaporated under high vacuum to give the title compound as the acetate salt (25 mg, 71%).

Workup

  1. customA reaction flask equipped with a stir bar
  2. customThe reaction mixture was sealed with a rubber septum
  3. customthe air was evacuated under house vacuum
  4. additionA balloon filled with hydrogen gas
  5. filtrationThe mixture was filtered through diatomaceous earth
  6. customthe filtrate was evaporated
  7. washThe residue was washed with 2 mL of ether and 2 mL of hexane
  8. customThe product was dried
  9. addition5 mL of acetic acid was added
  10. customThe acetic acid was evaporated under high vacuum

Sources & evidence

ORD record
ord-eaf869fbc77b4815aaae16b332f2a8f3
Source dataset
uspto-grants-2011_11
Patent number
US08063094B2

Reaction notes

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