Acetic Acid → HCID 59314256, compound

HRID 1047846Notes

Reaction equation

HRID 1047846 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][C:11]2([C:20]([OH:22])=[O:21])[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)=[O:9])=[C:6]([CH:23]=[C:24]([CH3:26])[CH3:25])[C:5]([CH3:27])=[CH:4][CH:3]=1.[C:28](O)(=[O:30])[CH3:29]>[Pd]>[C:28]([NH:1][C:2]1[C:7]([C:8]([NH:10][C:11]2([C:20]([OH:22])=[O:21])[CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:19]2)=[O:9])=[C:6]([CH:23]=[C:24]([CH3:25])[CH3:26])[C:5]([CH3:27])=[CH:4][CH:3]=1)(=[O:30])[CH3:29]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 59314397HCID 59314397, compound

Product 1

HCID 59314256HCID 59314256, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of (225) (48 mg, 0.1 mmol) in acetic acid (10 mL) is added the catalyst, Pd—C (5 wt. % Pd, 21 mg, 1% mmol) under argon. The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 55 psi, 90° C., overnight. The catalyst is removed by filtration through a pre-column (10 g silica gel) and washed with EtOH. The combined organic solution is concentrated in vacuo. The residue is purified by HPLC to give a pure product (226) as white solid (35 mg, 86%).

Workup

  1. customThe resulting reaction mixture
  2. custom55 psi, 90° C., overnight
  3. customThe catalyst is removed by filtration through a pre-column (10 g silica gel)
  4. washwashed with EtOH
  5. concentrationThe combined organic solution is concentrated in vacuo
  6. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-16aacba8d9184fd8851cf505c7bd4115
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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