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1,1'-Carbonyldiimidazole → [1-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-cyclohexyl]-acetic acid methyl ester

HRID 388456
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HRID 388456 반응식
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1([CH2:11][NH:12][C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH2:20])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24].N12CCCN=C1CCCCC2>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1([CH2:11][N:12]2[C:13](=[O:21])[C:14]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:20][C:23]2=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1
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참가 물질

6

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68724696{1-[(2-Amino-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl ester

생성물 1

HCID 68728121[1-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-cyclohexyl]-acetic acid methyl ester수율 99.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of {1-[(2-amino-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl ester (620 mg, 2.04 mmol) and 1,1′-carbonyldiimidazole (660 mg, 4.07 mmol) in THF (25 mL) is added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.6 mL, 4.01 mmol). The mixture is stirred at room temperature for 16 hours. The reaction mixture is diluted with EtOAc (100 mL) and is washed with H2O (50 mL×3). The organic layer is dried over sodium sulfate, and is concentrated to afford the desired [1-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-cyclohexyl]-acetic acid methyl ester (670 mg, 99%).

후처리

  1. washis washed with H2O (50 mL×3)
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationis concentrated

출처 및 근거

ORD 기록
ord-f351c29d370d43d88a5697eda6c80b17
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08377949B2

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