HCID 53261927, compound → HCID 53251081, compound

HRID 467951Notes

Reaction equation

HRID 467951 reaction equation
C(OC([NH:11][CH2:12][CH2:13][C:14]([NH:16][C@@H:17]([CH2:20][C:21]1[NH:25][CH:24]=[N:23][CH:22]=1)[CH2:18][OH:19])=[O:15])=O)C1C=CC=CC=1>[Pd].CO.O>[NH2:11][CH2:12][CH2:13][C:14]([NH:16][C@@H:17]([CH2:20][C:21]1[NH:25][CH:24]=[N:23][CH:22]=1)[CH2:18][OH:19])=[O:15]

Participants

4

Reactant 1

HCID 53261927HCID 53261927, compound

Product 1

HCID 53251081HCID 53251081, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

A round-bottom flask under inert atmosphere is loaded with 26 g of the oily product from Example 3, and 100 g of a 1:1 methanol/water mixture. The mixture is stirred to complete dissolution, then added with 2.6 g of 10% Pd/C. A washing cycle is carried out under nitrogen-vacuum, then the mixture is heated to 40° C. and hydrogen is slowly bubbled therein until complete disappearance of the starting product. The mixture is cooled to 30° C. and the catalyst is filtered off through a celite pad, washing twice with a methanol-water mixture. The solvent is evaporated off and the residue is repeatedly taken up with isobutanol and evaporated to obtain 9 g of a white solid.

Workup

  1. customhydrogen is slowly bubbled
  2. temperatureThe mixture is cooled to 30° C.
  3. filtrationthe catalyst is filtered off through a celite pad
  4. washwashing twice with a methanol-water mixture
  5. customThe solvent is evaporated off
  6. customevaporated

Sources & evidence

ORD record
ord-25f1e24f8a91477e9be155b2479de223
Source dataset
uspto-grants-2014_01
Patent number
US08623900B2

Reaction notes

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