Triphenylphosphine → {1-[4-(pentafluoro-lambda6-sulfanyl)phenyl]-1H-tetrazol-5-yl}methyl acetate

HRID 517729Notes

Reaction equation

HRID 517729 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:23][CH2:24][C:25](=O)[NH:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([F:38])([F:37])([F:36])([F:35])[F:34])=[CH:29][CH:28]=1)(=[O:22])[CH3:21].C[Si]([N:44]=[N+:45]=[N-:46])(C)C>C1COCC1.CCOC(C)=O>[C:20]([O:23][CH2:24][C:25]1[N:26]([C:27]2[CH:32]=[CH:31][C:30]([S:33]([F:38])([F:37])([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[N:46]=[N:45][N:44]=1)(=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 866918762-Oxo-2-{[4-(pentafluoro-lambda6-sulfanyl)phenyl]amino}ethyl acetate2×

Product 1

HCID 86691878{1-[4-(pentafluoro-lambda6-sulfanyl)phenyl]-1H-tetrazol-5-yl}methyl acetateYield 59%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triphenylphosphine (16.2 g, 61.9 mmol) and diisopropylazodicorboxylate (12.5 g, 61.8 mmol) were added to a solution of 2-oxo-2-{[4-(pentafluoro-λ6-sulfanyl)phenyl]amino}ethyl acetate (Intermediate 42, 8.50 g, 26.2 mmol) in THF (100 mL) at 0° C. and the mixture was stirred for 30 min. Trimethylsilyl azide (7.11 g, 61.7 mmol) was added dropwise at room temperature and the mixture was heated to reflux for 4 hr. The reaction mixture was diluted with EtOAc and washed with ice-water and brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude product (5.32 g). This was used for the next step without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hr
  3. washwashed with ice-water and brine solution
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1529a46bd46a40998a8e12d2b64ce543
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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