Sodium hydride → 6-(3-Acetyl-5-chloro-2-methoxy-6-methylphenyl)morpholin-3-one

HRID 1499943노트

반응식

HRID 1499943 반응식
[C:1]([C:4]1[C:5]([O:20][CH3:21])=[C:6]([CH:12]([OH:19])[CH2:13][NH:14][C:15](=[O:18])[CH2:16]Cl)[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2].[H-].[Na+]>O1CCCC1>[C:1]([C:4]1[C:5]([O:20][CH3:21])=[C:6]([CH:12]2[CH2:13][NH:14][C:15](=[O:18])[CH2:16][O:19]2)[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 86677858N-[2-(3-Acetyl-5-chloro-2-methoxy-6-methylphenyl)-2-hydroxyethyl]-2-chloroacetamide

생성물 1

HCID 866778596-(3-Acetyl-5-chloro-2-methoxy-6-methylphenyl)morpholin-3-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of N-[2-(3-acetyl-5-chloro-2-methoxy-6-methylphenyl)-2-hydroxyethyl]-2-chloroacetamide (170 mg, 0.50 mmol) (single enantiomer from step 3) in tetrahydrofuran (4 mL) cooled at 0° C., a mixture of sodium hydride (60% dispersion in mineral oil; 39 mg, 1.0 mmol) was added and stirred for 1 hour. The reaction was quenched with water and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, and concentrated to give the crude residue as a single enantiomer, 61 mg, 41%. LCMS calculated for C14H17ClNO4 (M+H)+: m/z=298.1; found: 298.1.

후처리

  1. additionwas added
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8c9a8103d40b40b783622f461d92dafe
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199982B2

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