Hydrochloric Acid → HCID 178431647, compound

HRID 2405693Notes

Reaction equation

HRID 2405693 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[C:25]([CH3:27])([CH3:26])[O:24][C:23]([NH:28][C:29]45[CH2:36][CH:35]6[CH2:37][C:31]([C:38](=[O:40])[NH2:39])([CH2:32][CH:33]4[CH2:34]6)[CH2:30]5)=[N:22][S:21]3(=[O:42])=[O:41])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)CCC.[H][H].Cl>CO.[Pd]>[CH3:26][C:25]1([CH3:27])[O:24][C:23]([NH:28][C:29]23[CH2:36][CH:35]4[CH2:37][C:31]([C:38]([NH2:39])=[O:40])([CH2:32][CH:33]2[CH2:34]4)[CH2:30]3)=[N:22][S:21](=[O:41])(=[O:42])[C@@H:20]1[C:17]1[CH:16]=[CH:15][C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 178418361HCID 178418361, compoundHCID 178451743HCID 178451743, compound

Product 1

HCID 178431647HCID 178431647, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-{4-[(R)-2-(2-carbamoylhexahydro-2,5-methanopentalen-3a-ylamino)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda*6*-[1,4,3]oxathiazin-5-yl]-phenyl}-3,6-dihydro-2H-pyridine-1-carboxylic acid butyl ester (100 mg) in methanol (10 mL) was admixed with palladium on carbon (10%, 100 mg) and the mixture was stirred in a hydrogen atmosphere for 1.5 h. The mixture was filtered and concentrated. The residue was dissolved in 5 mL of dichloromethane, and 1 mL of trifluoroacetic acid was added. After stirring at room temperature for 1 h, the solvent was removed under reduced pressure and TFA ester formed was cleaved by treatment with 1 N HCl. Extraction with ethyl acetate gave the crude product, which was used without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 5 mL of dichloromethane
  4. addition1 mL of trifluoroacetic acid was added
  5. customthe solvent was removed under reduced pressure and TFA ester
  6. customformed
  7. extractionExtraction with ethyl acetate

Sources & evidence

ORD record
ord-26d6ff5b26b74fc883133d67b5516d33
Source dataset
uspto-grants-2014_08
Patent number
US08809324B2

Reaction notes

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