Water → HCID 178524875, 화합물

HRID 2169250노트

반응식

HRID 2169250 반응식
C([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2([C:29]3[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=3[Cl:36])[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:9]=1)=[O:7])(C)(C)C.O.C(OCC)(=O)C>O1CCCC1.O.CCCCCC>[CH2:15]([O:14][C:13]1[C:8]([C:6]([OH:7])=[O:5])=[N:9][C:10]([CH2:23][C:24]2([C:29]3[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=3[Cl:36])[CH2:25][CH2:26][CH2:27][CH2:28]2)=[N:11][C:12]=1[OH:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 178450815HCID 178450815, 화합물

생성물 1

HCID 178524875HCID 178524875, 화합물수율 72.5%

시약·촉매·용매 2

HCID 8058Hexane용매HCID 21881883Oxolane--water (1/1)용매

실험 절차

To a stirred solution of 5-benzyloxy-2-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (204) (2.0 g, 3.788 mmol) in tetrahydrofuran-H2O (2:1) (30 mL) Li(OH).H2O (1.591 g, 37.88 mmol) was added, then the reaction mixture was stirred under reflux for 16 h. Silica thin layer chromatography was performed (40% ethyl acetate in hexane, Rf=0.1). After completion of the reaction, volatiles were removed, the reaction mixture was diluted with water, the pH was adjusted to pH ˜7 with 1N HCl, then the reaction mixture was extracted with ethyl acetate. The organic part was dried with Na2SO4, then concentrated to get pure 5-benzyloxy-2-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid (205) (1.3 g, 72.5%) as a white solid.

후처리

  1. temperatureunder reflux for 16 h
  2. customAfter completion of the reaction, volatiles
  3. customwere removed
  4. additionthe reaction mixture was diluted with water
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. dry with materialThe organic part was dried with Na2SO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8c86fbbb53594578a26687c84a81775b
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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