Ethyl Acetate → HCID 59855122, compound

HRID 2375732Notes

Reaction equation

HRID 2375732 reaction equation
[CH3:1][N:2]1[C:6]([C@H:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18]CC3C=C(C4C=CC(C(F)(F)F)=CC=4)C=CC=3)=[CH:14][CH:13]=2)[CH2:8][C:9]([OH:11])=[O:10])=[N:5][CH:4]=[N:3]1.[CH3:36]COC(C)=O>>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([C@@H:7]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][N:5]=2)[CH2:8][C:9]([O:11][CH3:36])=[O:10])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 15603738HCID 15603738, compound

Product 1

HCID 59855122HCID 59855122, compound

Procedure

Methyltriazole 5 (2.78 g, 5.61 mmol) was dissolved in 50 mL of EtOAc, and nitrogen was bubbled through the solution for 5 minutes. 1 g of palladium on carbon (5 wt. %, wet contains 50% water) was added, and a hydrogen balloon was attached. After 8 hours, the mixture was filtered through a plug of silica with 10% MeOH in EtOAc. The organic layer was concentrated under reduced pressure and partitioned between acetonitrile (100 mL) and hexane (50 mL). The acetonitrile layer was washed with hexane (4×50 mL). The acetonitrile layer was concentrated under reduced pressure to afford (S)-methyl 3-(4-hydroxyphenyl)-3-(2-methyl-2H-1,2,4-triazol-3-yl)propanoate 6.1 (1.30 g, 4.99 mmol) as a colorless oil. MS ESI (pos.) m/e: 262.4 (M+H)+.

Workup

  1. customnitrogen was bubbled through the solution for 5 minutes
  2. addition1 g of palladium on carbon (5 wt. %, wet contains 50% water) was added
  3. filtrationthe mixture was filtered through a plug of silica with 10% MeOH in EtOAc
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. custompartitioned between acetonitrile (100 mL) and hexane (50 mL)
  6. washThe acetonitrile layer was washed with hexane (4×50 mL)
  7. concentrationThe acetonitrile layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-83b782f38e824f8cbe9f7575719becc2
Source dataset
uspto-grants-2008_12
Patent number
US07465804B2

Reaction notes

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