Trimethylsilyldiazomethane → HCID 18466584, compound

HRID 2229149Notes

Reaction equation

HRID 2229149 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][C:15]=2[F:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][Si](C=[N+]=[N-])(C)C>CO.C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:25])=[O:22])=[CH:16][C:15]=2[F:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 18466562HCID 18466562, compound

Product 1

HCID 18466584HCID 18466584, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To 2-(4-{4-[(t-butyl)oxycarbonyl]piperazinyl}-3-fluorophenyl)acetic acid (0.3 g, 1.0 mmol) in 2 mL methanol and 7 mL benzene was added trimethylsilyidiazomethane (0.65 mL, 1.30 mmol). After stirring at ambient temperature for 1 hour, the reaction mixture was concentrated to provide 0.36 g (99%) of the title compound. 1H NMR (CDCl3; 300 MHz) δ7.00 (m, 2H), 6.90 (t, J=8.3 Hz, 1H), 3.71 (s, 3H), 3.61 (t, J=4.9 Hz, 4H), 3.57 (s, 2H), 3.02 (t, J=5.0 Hz, 4H), 1.50 (s, 9H); ESI (M+H)+=353.

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-599cb0507be545199b519c7325d0e47c
Source dataset
uspto-grants-2002_07
Patent number
US06420349B1

Reaction notes

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