Hydrochloric Acid → HCID 178461160, compound

HRID 1510149Notes

Reaction equation

HRID 1510149 reaction equation
[CH:1]1([NH:7][C:8]2[C@:12]3([CH2:17][CH2:16][N:15](C(OCC4C=CC=CC=4)=O)[C@@H:14]([CH3:28])[CH2:13]3)[N:11]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=3)[C:10](=[O:36])[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[OH-].[Na+]>CO.[OH-].[OH-].[Pd+2]>[CH:1]1([NH:7][C:8]2[C@:12]3([CH2:17][CH2:16][NH:15][C@@H:14]([CH3:28])[CH2:13]3)[N:11]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=3)[C:10](=[O:36])[N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178461164HCID 178461164, compound

Product 1

HCID 178461160HCID 178461160, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Benzyl (5R,7S)-4-(cyclohexylamino)-1-(3-fluorophenyl)-7-methyl-2-oxo-1,3,8-triazaspiro[4.5]dec-3-ene-8-carboxylate (27.9 g, 0.057 moles) was suspended in MeOH (˜200 mL) and methanolic HCl was added until the solids all went into solution. Pd(OH)2 (4 g, moisture content 60%) was added and the reaction was flushed with hydrogen and kept under a hydrogen balloon. The reaction was stirred at room temperature for 30 min. The reaction was evacuated and recharged with H2 once to remove CO2. The reaction was filtered through celite and concentrated, then the free base was obtained by portioning between CHCL3 and 1 N NaOH. The organic was dried over MgSO4, filtered and evaporated to give the product.

Workup

  1. customthe reaction was flushed with hydrogen
  2. customThe reaction was evacuated
  3. customto remove CO2
  4. filtrationThe reaction was filtered through celite and
  5. concentrationconcentrated
  6. customthe free base was obtained
  7. dry with materialThe organic was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customto give the product

Sources & evidence

ORD record
ord-62fbc73e4615427082f0281763f9929e
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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