HCID 13649256, compound → HCID 13649274, compound

HRID 1200152Notes

Reaction equation

HRID 1200152 reaction equation
[CH3:1][C:2]([NH:10][C:11](=[O:31])[C@@H:12]([NH:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:13][O:14]CC1C=CC=CC=1)([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H]>C(O)(=O)C.C(O)C.[Pd]>[CH3:9][C:2]([NH:10][C:11](=[O:31])[C@@H:12]([NH:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:13][OH:14])([CH3:1])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 13649256HCID 13649256, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13649274HCID 13649274, compoundYield 89.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

2.0 g of (2S)-N-(α,α-dimethylbenzyl)-2-benzoylamino-3-benzyloxypropionamide (prepared as described in Example 5) was catalytically reduced with hydrogen gas in the presence of 0.4 g of 10% w/w palladium-on-carbon in a mixture of 4 ml of acetic acid and 60 ml of ethanol. After completion of the reaction, the catalyst was filtered off and the solvent was distilled off. Recrystallization of the resulting residue from acetic acid and hexane gave 1.4 g of the title compound, melting at 152°-153° C.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. distillationthe solvent was distilled off
  4. customRecrystallization of the resulting residue from acetic acid and hexane

Sources & evidence

ORD record
ord-1aa2e2289df74c1fb4b1eb28fa9d515e
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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