HCID 71186455, compound → HCID 71204704, compound

HRID 712894Notes

Reaction equation

HRID 712894 reaction equation
[F:1][C@@H:2]1[CH2:6][N:5](CC2C=CC=C(C(F)(F)F)C=2)[C@@H:4]([C:18]([NH:20][C@H:21]([C:23]2[CH:31]=[CH:30][C:26]([C:27]([O-:29])=[O:28])=[CH:25][CH:24]=2)[CH3:22])=[O:19])[CH2:3]1.[Li+]>CO.Cl.[Pd]>[F:1][C@@H:2]1[CH2:6][NH:5][C@@H:4]([C:18]([NH:20][C@H:21]([C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=2)[CH3:22])=[O:19])[CH2:3]1

Participants

5

Reactant 1

HCID 71186455HCID 71186455, compound

Product 1

HCID 71204704HCID 71204704, compoundYield 74.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A suspension of lithium 4-((S)-1-((2R,4S)-4-fluoro-1-(3-(trifluoromethyl)benzyl)pyrrolidine-2-carboxamido)ethyl)benzoate (D161) (47 mg) and 10% w Pd/C (5 mg) in MeOH (5 ml) and 1M HCl (0.5 ml) was stirred under a constant current of H2 for 3 hrs. Catalyst was filtered off and solvent evaporated to afford a residue which was triturated with cHex and filtered to afford the title compound (D162) (22 mg).

Workup

  1. filtrationCatalyst was filtered off
  2. customsolvent evaporated
  3. customto afford a residue which
  4. customwas triturated with cHex
  5. filtrationfiltered

Sources & evidence

ORD record
ord-af63ec8861f84ebe81c2fdbd966a518a
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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