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

HRID 1643284노트

반응식

HRID 1643284 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-4696ee3eb0d7433dacfa4d627db1b57b
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119692B2

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