Hydroxylamine → (S)-2-((R)-2-(4-Fluoro-3-methylphenyl)-2-methoxyethyl)-N-hydroxypent-4-enamide

HRID 1643284Notes

Reaction equation

HRID 1643284 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([O:18][CH3:19])[CH2:9][C@H:10]([CH2:15][CH:16]=[CH2:17])[C:11](OC)=[O:12])=[CH:4][C:3]=1[CH3:20].C1COCC1.[NH2:26][OH:27].[C-]#N.[K+]>O.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([O:18][CH3:19])[CH2:9][C@H:10]([CH2:15][CH:16]=[CH2:17])[C:11]([NH:26][OH:27])=[O:12])=[CH:4][C:3]=1[CH3:20]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 8028TetrahydrofuranHCID 9032Potassium CyanideHCID 59568824(S)-Methyl 2-((R)-2-(4-fluoro-3-methylphenyl)-2-methoxyethyl)pent-4-enoate

Product 1

HCID 59568790(S)-2-((R)-2-(4-Fluoro-3-methylphenyl)-2-methoxyethyl)-N-hydroxypent-4-enamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(S)-Methyl 2-((R)-2-(4-fluoro-3-methylphenyl)-2-methoxyethyl)pent-4-enoate (50 mg) was dissolved into 1 mL of a mixture of THF, methanol, and 50% NH2OH in H2O (2:2:1) and to this solution was added 2 mg KCN. The reaction was stirred for 3 days at room temperature and then quenched by the addition of 1M HCl (10 mL). The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2×10 mL) before being concentrated under reduced pressure. The product was isolated by flash column chromatography eluting with 0% to 10% methanol/DCM to obtain the title compound (34 mg) as white solid.

Workup

  1. customquenched by the addition of 1M HCl (10 mL)
  2. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  3. washThe combined organic layers were washed with brine (2×10 mL)
  4. concentrationbefore being concentrated under reduced pressure
  5. customThe product was isolated by flash column chromatography
  6. washeluting with 0% to 10% methanol/DCM

Sources & evidence

ORD record
ord-4696ee3eb0d7433dacfa4d627db1b57b
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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