Hydroxylamine → (R)-6-(4-Fluoro-3-methylbenzyloxy)-2-(4-fluoro-3-methylphenoxy)-N-hydroxyhexanamide
Reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH3:32])[CH:26]=2)[C:13]([N:15]2[C@@H](C(C)C)COC2=O)=[O:14])=[CH:4][C:3]=1[CH3:35].C[OH:37].NO.[C-]#N.[K+]>C1COCC1.O>[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH3:32])[CH:26]=2)[C:13]([NH:15][OH:37])=[O:14])=[CH:4][C:3]=1[CH3:35]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (S)-3-((R)-6-(4-fluoro-3-methylbenzyloxy)-2-(4-fluoro-3-methylphenoxy)hexanoyl)-4-isopropyloxazolidin-2-one (100 mg, 0.20 mmol) dissolved in 2 mL of THF, methanol, and 50 wt % NH2OH in H2O (2:2:1) was added KCN (4.0 mg, 0.06 mmol). The resulting mixture stirred for 3 days at room temperature. The reaction was quenched by the addition of 1M aqueous HCl (10 mL) and the resulting mixture extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (2×5 mL). The product was isolated by flash column chromatography eluting with 0% to 10% methanol/DCM to give the title compound (54.2 mg) as colorless oil.
Workup
- customThe reaction was quenched by the addition of 1M aqueous HCl (10 mL)
- extractionthe resulting mixture extracted with ethyl acetate (3×10 mL)
- washThe combined organic layers were washed with brine (2×5 mL)
- customThe product was isolated by flash column chromatography
- washeluting with 0% to 10% methanol/DCM
Sources & evidence
- ORD record
- ord-3a31da602e3945f29029b08a105a5d14
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879911B2
Reaction notes
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