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

HRID 1643284ノート

反応式

HRID 1643284 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-4696ee3eb0d7433dacfa4d627db1b57b
出典データセット
uspto-grants-2012_02
特許番号
US08119692B2

反応ノート

読み込み中…