Ethanol → HCID 131726547, compound

HRID 853806Notes

Reaction equation

HRID 853806 reaction equation
[C:1]([O:4][NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25](=[NH:31])[NH:26]OC(=O)C)=[CH:21][CH:20]=3)=[CH:17][CH:18]=2)=[CH:10][N:9]=1)=[NH:7])(=[O:3])[CH3:2].C(O)C>C(O)(=O)C.[Pd]>[C:1]([OH:4])(=[O:3])[CH3:2].[C:25]([C:22]1[CH:21]=[CH:20][C:19]([C:16]2[O:15][C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:6]([NH2:7])=[NH:5])=[N:9][CH:10]=3)=[CH:18][CH:17]=2)=[CH:24][CH:23]=1)(=[NH:26])[NH2:31]

Participants

5

Reactant 2

HCID 702EthanolHCID 178476699HCID 178476699, compound

Product 1

HCID 131726547HCID 131726547, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Continuing with Scheme 3, to a solution of 19 (380 mg, 0.90 mmol) in glacial acetic acid (13 mL), and ethanol (25 mL) was added 10% palladium on carbon (120 mg). The mixture was placed on Parr hydrogenation apparatus at 50 psi for 4 h at room temperature. The mixture was filtered through HYFLO® matrix (available from Word Minerals Corporation of Santa Barbara, Calif., United States of America) and the filter pad washed with water. The filtrate was evaporated under reduced pressure and the precipitate was collected and washed with ether to give 20, in 68% yield, mp 266–268° C.dec.

Workup

  1. filtrationThe mixture was filtered through HYFLO® matrix (available from Word Minerals Corporation of Santa Barbara, Calif., United States of America)
  2. washthe filter pad washed with water
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe precipitate was collected
  5. washwashed with ether

Sources & evidence

ORD record
ord-b6cf539768d14fdfbcde0d4771b9a29d
Source dataset
uspto-grants-2007_08
Patent number
US07256203B2

Reaction notes

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