HCID 86588285, compound → HCID 69895788, compound

HRID 1385771Notes

Reaction equation

HRID 1385771 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:40])/[C:17](/[CH3:39])=[CH:18]/[CH:19]=[C:20](\[CH3:38])/[C:21]([N:23]1[CH2:27][CH2:26][CH2:25][C@@H:24]1[C:28]([O:30]CC1C=CC=CC=1)=[O:29])=[O:22])=[O:10])C1C=CC=CC=1.[H][H]>O1CCOCC1.[Pt](=O)=O>[C:28]([C@H:24]1[CH2:25][CH2:26][CH2:27][N:23]1[C:21](=[O:22])[CH:20]([CH3:38])[CH2:19][CH2:18][CH:17]([CH3:39])[C:16]([N:12]1[CH2:13][CH2:14][CH2:15][C@@H:11]1[C:9]([OH:10])=[O:8])=[O:40])([OH:30])=[O:29]

Participants

5

Reactant 2

HCID 86588285HCID 86588285, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69895788HCID 69895788, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 593 mg (1.09 mmol) (2E,4E)-(R)-1-[6-[(R)-2-benzyloxycarbonyl-pyrrolidin-1-yl]-2,5-dimethyl- 6-oxo-hexa-2,4-dienoyl]-pyrrolidine-2-carboxylic acid benzyl ester in 15 ml dioxane was stirred with 25 mg (0.11 mmol) platinum (IV) oxide under 1 atm of hydrogen for 72 h at room temperature. After filtration to remove the catalyst, the reaction mixture was concentrated in vacuo and azeotroped three times with chloroform on a rotary evaporator to remove last traces of dioxane, then triturated in ether to afford 400 mg (100%) of the title compound as a white foam. MS m/e (%): 369 (M+H+, 100).

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customazeotroped three times with chloroform
  5. customon a rotary evaporator
  6. customto remove last traces of dioxane
  7. customtriturated in ether

Sources & evidence

ORD record
ord-c4670c6fb9de4d649f8a7b392d9a15c2
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

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