HCID 18475838, compound → HCID 18475826, compound

HRID 2187877Notes

Reaction equation

HRID 2187877 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[NH:19][C:20](=[O:30])[CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:11][CH:10]=1)C1C=CC=CC=1>CCO.[Pd]>[C:26]([O:25][C:23]([NH:22][CH2:21][C:20]([NH:19][C:16]1[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([OH:8])[CH:18]=2)[CH:13]=[CH:14][CH:15]=1)=[O:30])=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 1

HCID 18475838HCID 18475838, compound

Product 1

HCID 18475826HCID 18475826, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-(7-benzyloxynaphthalen-1-yl)(tert-butoxycarbonylamino)acetamide, as described above in Step K, (1.22 g, 3.01 mmol) in EtOH (30 mL) was added 10% Pd-C on carbon (220 mg) and the reaction mixture was stirred under an atmosphere of hydrogen (ca. 1 atm) at ambient temperature for 18 hrs. The mixture was filtered through a pad of celite, washing with EtOH, and the filtrate was concentrated in vacuo to give a crude product. This was purified by flash column chromatography on silica, eluting with EtOAc, to yield the titled product as a pale solid.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashing with EtOH
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give a crude product
  5. customThis was purified by flash column chromatography on silica
  6. washeluting with EtOAc

Sources & evidence

ORD record
ord-36bc6fa6393f4a60be08cd089876f06a
Source dataset
uspto-grants-2002_06
Patent number
US06410534B1

Reaction notes

Loading…