Hydrochloric Acid → HCID 178431663, compound

HRID 339898Notes

Reaction equation

HRID 339898 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[C:25]([CH3:27])([CH3:26])[O:24][C:23]([NH:28][C@H:29]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=4[F:46])[CH2:30][CH2:31][O:32][Si](C(C)(C)C)(C)C)=[N:22][S:21]3(=[O:48])=[O:47])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.[H][H].Cl>CO.[Pd]>[CH3:26][C:25]1([CH3:27])[O:24][C:23]([NH:28][C@H:29]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[F:46])[CH2:30][CH2:31][OH:32])=[N:22][S:21](=[O:48])(=[O:47])[CH:20]1[C:17]1[CH:16]=[CH:15][C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 178418361HCID 178418361, compoundHCID 178451739HCID 178451739, compound

Product 1

HCID 178431663HCID 178431663, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-Boc-4-(4-{2-[(S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamino]-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda*6*-[1,4,3]oxathiazin-5-yl}phenyl)-3,6-dihydro-2H-pyridine (575 mg) in methanol (25 ml) was admixed with palladium on charcoal (10%, 260 mg) and 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 (91%), 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-1742fe77f1754501b5c3a37696cd389e
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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