Azidotrimethylsilane → HCID 86667780, compound

HRID 1484486Notes

Reaction equation

HRID 1484486 reaction equation
[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:12])[C:8]([F:11])([F:10])[F:9].C[Si](C)(C)O[CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1.[N:29]([Si](C)(C)C)=[N+:30]=[N-:31]>CC#N>[N:29]([CH:2]([O:1][CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:12])[C:8]([F:10])([F:11])[F:9])=[N+:30]=[N-:31]

Participants

5

Reactant 3

HCID 78378AzidotrimethylsilaneHCID 11126922Acetamide, 2,2,2-trifluoro-N-(4-oxobutyl)-HCID 22357954HCID 22357954, compound

Product 1

HCID 86667780HCID 86667780, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
-40 °C

Procedure

A solution of N-(4-oxobutyl)trifluoroacetamide (1.0 g; 5.5 mmol) and a catalytic amount of anhydrous ferric chloride (44 mg; 0.27 mmol) in anhydrous MeCN (6 mL) was cooled to −40° C. A solution of methyl 4-[(trimethylsilyloxy)methyl]benzoate (1.56 g; 6.6 mmol) and azidotrimethylsilane (0.94 g; 8.2 mmol) in MeCN (5 mL) was added dropwise to the cooled solution. The reaction mixture was stirred at −40° C. for 60 min and quenched with buffered phosphate saline (pH 7.2). The aqueous solution was extracted with Et2O. The organic layer was washed with brine, dried over MgSO4, filtrated and evaporated. The residue was purified by column chromatography (Hex:DCM:EtOAc 7:2:1) to provide methyl 4-[(1-azido-4-trifluoroacetamidobutoxy)methyl]benzoate in a yield of 0.95 g (46%).

Workup

  1. customquenched with buffered phosphate saline (pH 7.2)
  2. extractionThe aqueous solution was extracted with Et2O
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltrated
  6. customevaporated
  7. customThe residue was purified by column chromatography (Hex:DCM:EtOAc 7:2:1)

Sources & evidence

ORD record
ord-558b1c285e614d78846d308a4da819df
Source dataset
uspto-grants-2016_08
Patent number
US09422232B2

Reaction notes

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