Ethyl Acetate → HCID 59855122, compound

HRID 2246647Notes

Reaction equation

HRID 2246647 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 M13.6 (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 ACN (100 mL) and hexane (50 mL). The ACN layer was washed with hexane (4×50 mL). The ACN layer was concentrated under reduced pressure to afford (S)-methyl 3-(4-hydroxyphenyl)-3-(2-methyl-2H-1,2,4-triazol-3-yl)propanoate M13 (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 ACN (100 mL) and hexane (50 mL)
  6. washThe ACN layer was washed with hexane (4×50 mL)
  7. concentrationThe ACN layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f03482dee04c44e2accf3a68369dca37
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

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