Hydrochloride methanol → HCID 178490620, compound

HRID 366028Notes

Reaction equation

HRID 366028 reaction equation
C([NH:11][C:12](=[N:47]C(OCC1C=CC=CC=1)=O)[NH:13][CH2:14][CH2:15][CH2:16][C@H:17]([C:34]([NH:36][C@@H:37]([C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=1)[CH3:38])=[O:35])[NH:18][C:19](=[O:33])[CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(OCC1C=CC=CC=1)=O.[ClH:58].CO>CC(O)=O.[Pd]>[ClH:58].[C:21]1([CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:19]([NH:18][C@@H:17]([C:34]([NH:36][C@@H:37]([C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[CH3:38])=[O:35])[CH2:16][CH2:15][CH2:14][NH:13][C:12](=[NH:11])[NH2:47])=[O:33])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 21893726Hydrochloride methanolHCID 178490618HCID 178490618, compound

Product 1

HCID 178490620HCID 178490620, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

(R)-Nω,Nω '-bis(Cbz)-N2 -(diphenylacetyl)-(R)-N-[1-(4-methoxyphenyl)ethyl]-arginine amide (5.40 g; 7.10 mmol; from step (f) above) in HOAc (300 mL) was flushed with nitrogen prior to the addition of 10% Pd/C (w/w; 1.10 g). The heterogeneous solution was briefly flushed with hydrogen and then stirred under 1 atmosphere of hydrogen for 4 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 evaporated at reduced pressure to give the crude product. The crude acetate salt was dissolved in HCl/MeOH, treated with activated carbon, filtered, concentrated, and dried under vacuum at 55-60° C. for 5 hours to give the sub-title compound as an off-white solid (3.47 g).

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 evaporated at reduced pressure
  5. customto give the crude product
  6. additiontreated with activated carbon
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried under vacuum at 55-60° C. for 5 hours

Sources & evidence

ORD record
ord-ddbfa0a0c7df493092a9fd9416bd555d
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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