Ethyl Acetate → HCID 178450815, 화합물

HRID 2169249노트

반응식

HRID 2169249 반응식
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[C:10]1([CH2:15][C:16]([NH2:18])=[NH:17])[CH2:14][CH2:13][CH2:12][CH2:11]1.[C:19]([O:23][C:24](=[O:39])/[C:25](/O)=[C:26](\[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)/[C:27](O)=[O:28])([CH3:22])([CH3:21])[CH3:20].C(OCC)(=O)C>CO.CCCCCC>[C:19]([O:23][C:24]([C:25]1[C:26]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:27]([OH:28])[N:18]=[C:16]([CH2:15][C:10]2([C:4]3[CH:5]=[C:6]([Cl:9])[CH:7]=[CH:8][C:3]=3[Cl:2])[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:17]=1)=[O:39])([CH3:22])([CH3:20])[CH3:21]

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 86725882(E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl esterHCID 867258982-[1-(2,5-Dichlorophenyl)-cyclopentyl]-acetamidine hydrochloride

생성물 1

HCID 178450815HCID 178450815, 화합물수율 53.55%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8058Hexane용매

실험 절차

To a stirred solution of 2-[1-(2,5-dichlorophenyl)-cyclopentyl]-acetamidine hydrochloride (2=3) (2.0, 7.407 mmol) and (E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester (4) (3.422 g, 11.111 mmol) in methanol (50 mL) NaOMe (25% in methanol; 4.8 mL) was added dropwise at 0° C. and stirred at room temperature for 16 h. Silica thin layer chromatography was performed (40% ethyl acetate in hexane, Rf=0.6). The reaction mixture was quenched with HCl (1N; 5 mL), methanol was removed, the product was diluted with water and the mixture was extracted with ethyl acetate. The combined organic part was dried, the product was concentrated and the crude product was purified using a normal silica gel column using a gradient eluent of 10 to 40% ethyl acetate in hexane to get pure 5-benzyloxy-2-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (204) (2.1 g, 53.55%) as a yellow solid.

후처리

  1. customThe reaction mixture was quenched with HCl (1N; 5 mL), methanol
  2. customwas removed
  3. additionthe product was diluted with water
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe combined organic part was dried
  6. concentrationthe product was concentrated
  7. customthe crude product was purified

출처 및 근거

ORD 기록
ord-9208057309df4b7ab9ce11dc4a8ac5a6
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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