Hydroxyamine hydrochloride → 2-(2-Ethyl-[1,3]dioxolan-2-yl)-2-fluoro-N-hydroxyacetamide
Reaction equation
C[O:2][C:3](=O)[CH:4]([F:12])[C:5]1([CH2:10][CH3:11])[O:9][CH2:8][CH2:7][O:6]1.Cl.[NH2:15][OH:16].CO[Na]>N1C=CC=CC=1>[CH2:10]([C:5]1([CH:4]([F:12])[C:3]([NH:15][OH:16])=[O:2])[O:9][CH2:8][CH2:7][O:6]1)[CH3:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-(2-ethyl-[1,3]dioxolan-2-yl)fluoroacetic acid methyl ester (1.50 g, 7.80 mmol) and hydroxylamine hydrochloride (1.07 g, 15.6 mmol) were dissolved in pyridine (8 mL). MeONa (30% in MeOH, 3.94 mL, 15.6 mmol) was dropped slowly over 15 min. More pyridine (8 mL) was added. The mixture was stirred for 30 min, then filtered. AcOH (1 mL) was added to the filtrate. The mixture was stirred for 5 min, then the solvents were removed under reduced pressure. Purification by FC (MeOH/CH2Cl2 1:10) yielded the title compound (502 mg, 40%).
Workup
- filtrationfiltered
- additionAcOH (1 mL) was added to the filtrate
- stirringThe mixture was stirred for 5 min
- customthe solvents were removed under reduced pressure
- customPurification by FC (MeOH/CH2Cl2 1:10)
Sources & evidence
- ORD record
- ord-9c96e272269d434490d0cc1ca0de0521
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138340B2
Reaction notes
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