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Diphosgene → (S)-2-(7-methoxy-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-hexanoic acid methyl ester

HRID 388476
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HRID 388476 반응식
[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:9][C:10](=[O:20])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[NH2:19])[CH2:5][CH2:6][CH2:7][CH3:8].Cl[C:23](OC(Cl)(Cl)Cl)=[O:24]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([N:9]1[C:10](=[O:20])[C:11]2[C:12](=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[NH:19][C:23]1=[O:24])[CH2:5][CH2:6][CH2:7][CH3:8]
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참가 물질

5

반응물 2

HCID 10426DiphosgeneHCID 68729255(S)-2-(2-amino-4-methoxy-benzoylamino)-hexanoic acid methyl ester

생성물 1

HCID 68727308(S)-2-(7-methoxy-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-hexanoic acid methyl ester수율 209.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

To a solution of (S)-2-(2-amino-4-methoxy-benzoylamino)-hexanoic acid methyl ester (1.0 g, 3.50 mmol) in THF (30 mL) is added trichloromethyl chloroformate (325 mg, 1.64 mmol). The mixture is stirred at 90° C. for 4 hours. The reaction mixture is allowed to cool to room temperature, diluted with EtOAc (100 mL) and washed with H2O (50 mL×3). The organic layer is dried over sodium sulfate and concentrated to give (S)-2-(7-methoxy-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-hexanoic acid methyl ester (1.1 g, 98%).

후처리

  1. temperatureto cool to room temperature
  2. washwashed with H2O (50 mL×3)
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6c8c4fae3898424da30458e0ac2ac45b
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08377949B2

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