Ethyl Acetate → HCID 59855134, compound

HRID 731174Notes

Reaction equation

HRID 731174 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 M14.2 (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 ACN (10 mL) and hexane (5 mL). The ACN layer was washed with hexane (4×5 mL). The ACN layer was concentrated under reduced pressure to afford (S)-methyl 3-(4-hydroxyphenyl)-3 -(1-methyl-1H-tetrazol-5-yl)propanoate (M 14) (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 ACN (10 mL) and hexane (5 mL)
  6. washThe ACN layer was washed with hexane (4×5 mL)
  7. concentrationThe ACN layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fa0e4bc94c684c9fb5106a1947b82e12
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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