Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → (S)-2-sec-Butylamino-6-(2-methyl-2H-tetrazol-5-yl)-isonicotinic acid methyl ester

HRID 1436592Notes

Reaction equation

HRID 1436592 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[N:12][NH:13][N:14]=2)[N:7]=[C:6]([NH:15][C@H:16]([CH2:18][CH3:19])[CH3:17])[CH:5]=1.F[B-](F)(F)F.[CH3:26][O+](C)C>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[N:12][N:13]([CH3:26])[N:14]=2)[N:7]=[C:6]([NH:15][C@H:16]([CH2:18][CH3:19])[CH3:17])[CH:5]=1

Participants

4

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 68815560(S)-2-sec-Butylamino-6-(2H-tetrazol-5-yl)-isonicotinic acid methyl ester

Product 1

HCID 68814453(S)-2-sec-Butylamino-6-(2-methyl-2H-tetrazol-5-yl)-isonicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Treat a solution of (S)-2-sec-butylamino-6-(2H-tetrazol-5-yl)-isonicotinic acid methyl ester (350 mg, 1.26 mmol) in ethyl acetate (8 mL) with trimethyloxonium tetrafluoroborate at room temperature for 3 h. Dilute with ethyl acetate (50 mL) and wash with saturated sodium bicarbonate and saturated aqueous sodium chloride. Dry (sodium sulfate) and concentrate to give the title compound which is used directly in the next step without further purification.

Workup

  1. washwash with saturated sodium bicarbonate and saturated aqueous sodium chloride
  2. dry with materialDry (sodium sulfate)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-baab93735d0a4ff1bee9d49fb6a210bf
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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