Phosphorus oxychloride → 3-(5-tert-Butyl-isoxazol-3-ylcarbamoyl)-morpholine-4-carboxylic acid tert-butyl ester

HRID 336209

반응식

HRID 336209 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[O:20][N:19]=1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH:9]1[C:14](=[O:16])[NH:17][C:18]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[O:20][N:19]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-HCID 27601334-(tert-Butoxycarbonyl)morpholine-3-carboxylic acid

생성물 1

HCID 866604023-(5-tert-Butyl-isoxazol-3-ylcarbamoyl)-morpholine-4-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a cold (0° C.) solution of morpholine-3,4-dicarboxylic acid 4-tert-butyl ester (100 mg; 0.432 mmol) and 3-amino-5-t-butylisoxazole (58.9 mg; 0.42 mmol) in anhydrous pyridine (1.2 mL) is added phosphorous oxychloride (0.039 mL; 0.432 mmol). The reaction mixture is left stirring at room temperature for 1 hour. After this time, the reaction mixture is quenched with saturated NH4Cl aqueous solution and extracted with ethyl acetate twice. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using methanol/methylene chloride provides the title compound, m/z 354 [M+H+].

후처리

  1. waitThe reaction mixture is left
  2. customAfter this time, the reaction mixture is quenched with saturated NH4Cl aqueous solution
  3. extractionextracted with ethyl acetate twice
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-6942aa99a61e48f8a2405baa04cd22c5
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889670B2

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