HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triphenylphosphine → {1-[3-cyano-5-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl acetate

HRID 517716
Notes
Print preview

Reaction equation

HRID 517716 reaction equation
[C:1]([O:4][CH2:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([C:19]#[N:20])[CH:10]=1)=O)(=[O:3])[CH3:2].C[Si]([N:25]=[N+:26]=[N-:27])(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.CCOC(C)=O>[C:1]([O:4][CH2:5][C:6]1[N:8]([C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([C:19]#[N:20])[CH:10]=2)[N:27]=[N:26][N:25]=1)(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 66653997HCID 66653997, compound2×

Product 1

HCID 66654533{1-[3-cyano-5-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl acetateYield 90.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-{[3-cyano-5-(trifluoromethyl)phenyl]amino}-2-oxoethyl acetate (Intermediate 29, 3.38 g, 11.8 mmol) in tetrahydrofuran (100 mL) was added trimethylsilylazide (3.14 mL, 23.6 mmol), triphenylphosphine (6.20 g, 23.6 mmol) then di-isopropylazodicarboxylate (4.60 mL, 23.6 mmol). The reaction was warmed to 50° C. and stirred for 6 hours. The reaction was cooled and diluted with EtOAc (150 mL). The solution was washed with water (100 mL), passed through a hydrophobic frit and the solvent removed under vacuum. The residue was purified by silica chromatography (Biotage SP4, eluting 10% EtOAc in iso-hexane (4 column volumes) then a gradient from 10-35% EtOAc in iso-hexane (over 8 column volumes)) to yield the title compound as a yellow solid (3.33 g)

Workup

  1. temperatureThe reaction was cooled
  2. washThe solution was washed with water (100 mL)
  3. customthe solvent removed under vacuum
  4. customThe residue was purified by silica chromatography (Biotage SP4
  5. washeluting 10% EtOAc in iso-hexane (4 column volumes)

Sources & evidence

ORD record
ord-54583ebcb45e409bb56df18aef411072
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115132B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes