Water → 4-(3-Oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 895632노트

반응식

HRID 895632 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][C:23](O)=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.C(N(CC)CC)C.O>ClC(Cl)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH2:22][C:23]2=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 223807041-t-Butyloxycarbonyl-4-((2-carboxymethoxyphenyl)amino)piperidine

생성물 1

HCID 223806764-(3-Oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester수율 57.4%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

1-(tert-Butoxycarbonyl)-4-[(2-carboxymethoxyphenyl)amino]piperidine (351 mg) was dissolved in dichloroethane (7 ml), added with thionyl chloride (73 μl) and stirred at room temperature for 1.5 hours. The reaction mixture was added with triethylamine (0.28 ml) and further stirred at 40° C. for 2 hours. The reaction mixture was added with water (10 ml) and extracted twice with ethyl acetate (10 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=2:1) to obtain 191 mg of the title compound. Yield: 57%.

후처리

  1. stirringfurther stirred at 40° C. for 2 hours
  2. extractionextracted twice with ethyl acetate (10 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-e6e085b3ea8b47ef91d96662ebaf73db
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916822B2

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