HCID 86723607, compound → HCID 86723608, compound

HRID 590673Notes

Reaction equation

HRID 590673 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([C@@H:27]([CH3:30])[CH2:28][CH3:29])[C:7]([N:9]1[C@H:13]([C:14]([O:16]CC2C=CC=CC=2)=[O:15])[CH2:12][C@@H:11]2[CH2:24][CH2:25][CH2:26][C@H:10]12)=[O:8])=[O:4]>[Pd].C(O)C>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([C@@H:27]([CH3:30])[CH2:28][CH3:29])[C:7]([N:9]1[C@H:13]([C:14]([OH:16])=[O:15])[CH2:12][C@@H:11]2[CH2:24][CH2:25][CH2:26][C@H:10]12)=[O:8])=[O:4]

Participants

4

Reactant 1

HCID 86723607HCID 86723607, compound

Product 1

HCID 86723608HCID 86723608, compoundYield 117.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a 250 mL round bottom flask charged with a stirbar and (2S,3aS,6aS)-benzyl 1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)octahydrocyclopenta[b]pyrrole-2-carboxylate (19.53 g crude, assumed 35.49 mmol) was added 10% Palladium on carbon (3.55 g). Ethanol was poured over the mixture and the reaction mixture was evacuated and flushed with hydrogen gas three times. The suspension was stirred at room temperature under and atmosphere of hydrogen for 3 days. Upon completion, the reaction mixture was filtered through celite and concentrated to give (2S,3aS,6aS)-1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid (13.65 g, >99%). LCMS-ESI+ calc'd for C16H26N2O5: 327.18. Found: 327.13.

Workup

  1. customthe reaction mixture was evacuated
  2. customflushed with hydrogen gas three times
  3. filtrationUpon completion, the reaction mixture was filtered through celite and
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-da7dfc8c5b694ab8b1f416ae94913592
Source dataset
uspto-grants-2016_01
Patent number
US09233974B2

Reaction notes

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