HCID 68643361, compound → HCID 68417539, compound

HRID 271862Notes

Reaction equation

HRID 271862 reaction equation
[C:1]([CH2:9][NH:10][CH2:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:26]([O:28]CC3C=CC=CC=3)=[O:27])=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[C:1]([CH2:9][NH:10][CH2:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:26]([OH:28])=[O:27])=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68643361HCID 68643361, compound

Product 1

HCID 68417539HCID 68417539, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

58 mg (10% by mass) of 10% palladium-on-charcoal are introduced into a solution containing 580 mg of benzyl 3-{3′-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-tert-butoxycarbonylaminopropionate in 8 ml of ethyl acetate. After bubbling hydrogen into the solution for 16 h at ambient temperature and 2 h at 50° C., the reaction medium is filtered through Celite and the solvents are evaporated off. The residue obtained is purified by chromatography on a column of silica and eluted with a 3/7 heptane/ethyl acetate mixture. 300 mg of 3-{3′-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-tert-butoxycarbonylaminopropionic acid are obtained with a 61% yield. Melting point: 80° C.

Workup

  1. customAfter bubbling hydrogen into the solution for 16 h at ambient temperature
  2. filtration2 h at 50° C., the reaction medium is filtered through Celite
  3. customthe solvents are evaporated off
  4. customThe residue obtained
  5. customis purified by chromatography on a column of silica
  6. washeluted with a 3/7 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-8da387a7b8884e089bfcbf2875eea57b
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

Loading…