Ethyl Acetate → HCID 59855134, compound

HRID 2375733Notes

Reaction equation

HRID 2375733 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][N: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]=[N: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 15604067HCID 15604067, compound

Product 1

HCID 59855134HCID 59855134, compound

Procedure

Methyltetrazole 7 (413 mg, 0.833 mmol) was dissolved in 5 mL of EtOAc and nitrogen was bubbled through the solution for 5 minutes. Palladium on carbon (200 mg, 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 (10 mL) and hexane (5 mL). The acetonitrile layer was washed with hexane (4×5 mL). The acetonitrile layer was concentrated under reduced pressure to afford (s)-methyl 3-(4-hydroxyphenyl)-3-(1-methyl-1H-tetrazol-5-yl)propanoate (8.1) (203 mg, 0.775 mmol) as a colorless oil.

Workup

  1. customnitrogen was bubbled through the solution for 5 minutes
  2. additionPalladium on carbon (200 mg, 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 (10 mL) and hexane (5 mL)
  6. washThe acetonitrile layer was washed with hexane (4×5 mL)
  7. concentrationThe acetonitrile layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-64a352a00bf84cb28461601a9f00ccf4
Source dataset
uspto-grants-2008_12
Patent number
US07465804B2

Reaction notes

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