tert-butyl (3R,5E)-3-({[(1S)-2,2-dimethyl-1-(benzyloxycarbonyl)propyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]hex-5-enoate → tert-butyl (3R)-3-({[(1S)-1-(carboxy)-2,2-dimethylpropyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]hexanoate

HRID 1700992Notes

Reaction equation

HRID 1700992 reaction equation
[CH3:1][C:2]([CH3:43])([CH3:42])[C@H:3]([NH:14][C:15]([C@H:17]([CH2:26]/[CH:27]=[CH:28]/[C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:31]([CH3:41])[CH:30]=1)[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])[C:4]([O:6]CC1C=CC=CC=1)=[O:5]>C(O)C.O.[Pd]>[CH3:1][C:2]([CH3:43])([CH3:42])[C@H:3]([NH:14][C:15]([C@H:17]([CH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:31]([CH3:41])[CH:30]=1)[CH2:18][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[O:16])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 59875769tert-butyl (3R,5E)-3-({[(1S)-2,2-dimethyl-1-(benzyloxycarbonyl)propyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]hex-5-enoate

Product 1

HCID 59875725tert-butyl (3R)-3-({[(1S)-1-(carboxy)-2,2-dimethylpropyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]hexanoateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19096565Water ethanolSolvent

Procedure

A solution of tert-butyl (3R,5E)-3-({[(1S)-2,2-dimethyl-1-(benzyloxycarbonyl)propyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]hex-5-enoate (2.205 g, 3.78 mmol) in ethanol/water=10:1 (44 mL) was hydrogenated over 10% palladium on charcoal at 3 bar and room temperature for 6 h. The mixture was filtered through Arbocel filter aid, washing well with ethanol. The filtrate was concentrated under reduced pressure. The residue was dissolved in toluene and evaporated (three times), dissolved in ether and evaporated (twice), and finally dissolved in ether and precipitated as an oil by the addition of hexane. Removal of the solvent under reduced pressure gave tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-(carboxy)propyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]hexanoate (1.817 g, 97%) as a colourless foam, m.p. 51-56° C.

Workup

  1. filtrationThe mixture was filtered through Arbocel
  2. filtrationfilter aid
  3. washwashing well with ethanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in toluene
  6. customevaporated (three times)
  7. dissolutiondissolved in ether
  8. customevaporated (twice), and
  9. dissolutionfinally dissolved in ether
  10. customprecipitated as an oil by the addition of hexane
  11. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-fa7abc67527d421dbd4597d9fd01cc37
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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