HCID 54305718, compound → HCID 54572570, compound

HRID 1638820Notes

Reaction equation

HRID 1638820 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]([CH2:17][C:18]#[N:19])([CH:11]1[C:15](=[O:16])[O:14][CH2:13][CH2:12]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H][H]>C(O)(=O)C.[Pt](=O)=O>[CH2:1]([O:3][C:4]([C:5]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:17][CH2:18][NH:19][C:15](=[O:16])[CH:11]1[CH2:12][CH2:13][OH:14])=[O:20])[CH3:2]

Participants

5

Reactant 2

HCID 54305718HCID 54305718, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54572570HCID 54572570, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 4.35 g (0.015 mol) of the cyanodiester from Example 5 in 100 mL of glacial acetic acid was added 150 mg of platinum (IV) oxide, and the mixture was agitated under hydrogen (60 psi) until hydrogen uptake had ceased. The mixture was filtered and the acetic acid was removed under reduced pressure (Ca. 0.5 mm) at 30°-35° C. To the oily residue (containing a trace amount of acetic acid) was added 300 mL of chloroform and the mixture was stirred at room temperature for 48 h. The solvent was removed in vacuo and the residue was triturated in pet ether and filtered. The resultant solid was subjected to flash chromatography (silica, 9:1 EtOAc/MeOH). The major isolated compound was recrystallized in CHCl3 /hexane to give 3.54 g (80%) of white solid: mp 120°-121° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe acetic acid was removed under reduced pressure (Ca. 0.5 mm) at 30°-35° C
  3. additionTo the oily residue (containing a trace amount of acetic acid)
  4. additionwas added 300 mL of chloroform
  5. customThe solvent was removed in vacuo
  6. customthe residue was triturated in pet ether
  7. filtrationfiltered
  8. customThe major isolated compound was recrystallized in CHCl3 /hexane

Sources & evidence

ORD record
ord-24b5bc83009041f58f67e29490c99102
Source dataset
uspto-grants-1989_11
Patent number
US04880924

Reaction notes

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