HCID 57947815, compound → HCID 57947627, compound

HRID 409884Notes

Reaction equation

HRID 409884 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]([NH:13][C:14](=[O:40])[O:15][CH2:16][C@@H:17]([N:26]([CH3:39])[C:27]([NH:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:32]=3[Cl:38])=[O:28])[CH2:18][C:19]([F:25])([F:24])[CH2:20][N:21]=[N+]=[N-])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]([NH:13][C:14](=[O:40])[O:15][CH2:16][C@@H:17]([N:26]([CH3:39])[C:27]([NH:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:32]=3[Cl:38])=[O:28])[CH2:18][C:19]([F:24])([F:25])[CH2:20][NH2:21])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 57947815HCID 57947815, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57947627HCID 57947627, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of (S)-5-azido-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-4,4-difluoropentyl 3-(3-fluorophenyl)isoxazol-5-ylcarbamate (0.35 g, 0.6 mmol) in MeOH (2 mL), was added 10% Pd/C (0.1 g). The mixture was transferred to an autoclave reactor, charged with 10 psi of hydrogen, and stirred for 10 min. The catalyst was filtered off and the filtrate was concentrated. The residue was purified on RP-HPLC using a mixture of acetonitrile and H2O with 0.1% TFA. The elute was washed with saturated NaHCO3. The organic layer was concentrated to give (S)-5-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-4,4-difluoropentyl 3-(3-fluorophenyl)isoxazol-5-ylcarbamate (0.18 g, 54%) as a white solid. LRMS (M+H+) m/z 558.1.

Workup

  1. customThe mixture was transferred to an autoclave reactor
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified on RP-HPLC
  5. additiona mixture of acetonitrile and H2O with 0.1% TFA
  6. washThe elute was washed with saturated NaHCO3
  7. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-bf89306a4b8241fcbfb9e75784f6fce9
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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