carbonic acid (2S,4S)-2-tert-butylcarbonylamino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-5-methyl-hexylester tert-butyl ester → carbonic acid (2S,4S)-2-tert-butylcarbonylamino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-5-methyl-hexylester tert-butyl ester

HRID 1099323Notes

Reaction equation

HRID 1099323 reaction equation
[C:1]([O:5][C:6](=[O:38])[O:7][CH2:8][C@@H:9]([NH:31][C:32]([C:34]([CH3:37])([CH3:36])[CH3:35])=[O:33])[CH2:10][C@H:11]([C:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=1)[CH:12]([CH3:14])[CH3:13])([CH3:4])([CH3:3])[CH3:2]>C(O)C.C(O)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:38])[O:7][CH2:8][C@@H:9]([NH:31][C:32]([C:34]([CH3:35])([CH3:37])[CH3:36])=[O:33])[CH2:10][C@H:11]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=1)[CH:12]([CH3:13])[CH3:14])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 66813799carbonic acid (2S,4S)-2-tert-butylcarbonylamino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-5-methyl-hexylester tert-butyl ester

Product 1

HCID 66813894carbonic acid (2S,4S)-2-tert-butylcarbonylamino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-5-methyl-hexylester tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18476134Acetic acid ethanolSolvent

Procedure

Carbonic acid (2S,4S)-2-tert-butylcarbonylamino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-5-methyl-hexylester tert-butyl ester (2.67 g) is dissolved in 25 mL of a mixture of ethanol/acetic acid, 2/1 at room temperature. Palladium metal, 10% on charcoal (0.3 g) is added and the suspension placed under an atmosphere of hydrogen at a pressure of 5 bar. Hydrogenation is continued for 3 days at 50° C. with periodic addition of more catalyst. The reaction mixture is filtered and the solvent removed to give an oil. The oil is purified by chromatography on silica-gel eluting with hexane/ethyl acetate mixtures. The product fractions are combined and the solvent is removed to give the title compound as an oil.

Workup

  1. additionHydrogenation is continued for 3 days at 50° C. with periodic addition of more catalyst
  2. filtrationThe reaction mixture is filtered
  3. customthe solvent removed
  4. customto give an oil
  5. customThe oil is purified by chromatography on silica-gel
  6. washeluting with hexane/ethyl acetate mixtures
  7. customthe solvent is removed

Sources & evidence

ORD record
ord-614a5370ba9443a7acd221de91e6de13
Source dataset
uspto-grants-2012_03
Patent number
US08143416B2

Reaction notes

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