Hydrochloric Acid → HCID 131722026, compound

HRID 366027Notes

Reaction equation

HRID 366027 reaction equation
C([NH:11][CH2:12][CH2:13][CH2:14][C@H:15]([C:32]([NH:34][C@@H:35]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)[CH3:36])=[O:33])[NH:16][C:17](=[O:31])[CH:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(OCC1C=CC=CC=1)=O.Cl>CO.[Pd]>[C:19]1([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17]([NH:16][C@@H:15]([C:32]([NH:34][C@@H:35]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[CH3:36])=[O:33])[CH2:14][CH2:13][CH2:12][NH2:11])=[O:31])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131722027HCID 131722027, compound

Product 1

HCID 131722026HCID 131722026, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (R)-N5 -(Cbz)-N2 -(Diphenylacetyl)-(R)-N-[1-(4-methoxy-phenyl)ethyl]ornithine amide (5.7 g; 9.6 mmol; from step (d) above) and HCl (2 N; 6 mL) in MeOH (200 mL) was flushed with nitrogen prior to the addition of 10% Pd/C (w/w; 530 mg). The heterogeneous solution was briefly flushed with hydrogen and then stirred under 1 atmosphere of hydrogen for 3 hours. When the deprotection was complete, as determined by TLC analysis, the solution was filtered through a pad of Celite to remove the catalyst. The filtrate was then evaporated at reduced pressure to give the crude product. The residue from evaporation of the filtrate was dissolved in water (300 mL) and washed with diethyl ether (2×50 mL). The aqueous layer was adjusted to pH 12 with concentrated NH4OH, then extracted with EtOAc (3×200 mL). The combined organic extracts were washed with brine (200 mL), then dried (Na2SO4) and filtered. The filtrate was evaporated at reduced pressure to give 4.2 g (95%) of the sub-title compound (free base) as a white solid.

Workup

  1. customThe heterogeneous solution was briefly flushed with hydrogen
  2. filtrationthe solution was filtered through a pad of Celite
  3. customto remove the catalyst
  4. customThe filtrate was then evaporated at reduced pressure
  5. customto give the crude product
  6. customThe residue from evaporation of the filtrate
  7. dissolutionwas dissolved in water (300 mL)
  8. washwashed with diethyl ether (2×50 mL)
  9. extractionextracted with EtOAc (3×200 mL)
  10. washThe combined organic extracts were washed with brine (200 mL)
  11. dry with materialdried (Na2SO4)
  12. filtrationfiltered
  13. customThe filtrate was evaporated at reduced pressure

Sources & evidence

ORD record
ord-83c1c0507ef848c480ab99b3993428d3
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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