Ethyl Acetate → HCID 178524873, 화합물

HRID 2169467노트

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HRID 2169467 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]=[CH:33][CH:32]=[CH:31][N:30]=3)[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:9]=1)=[O:7])(C)(C)C.O[Li].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]=[CH:33][CH:32]=[CH:31][N:30]=3)[CH2:25][CH2:26][CH2:27][CH2:28]2)=[N:11][C:12]=1[OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 178450813HCID 178450813, 화합물

생성물 1

HCID 178524873HCID 178524873, 화합물수율 87.3%

시약·촉매·용매 2

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

실험 절차

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (436) (1.2 g, 2.60 mmol) in tetrahydrofuran-water (2:1; 24 mL), LiOH.H2O (1.09 g, 26.03 mmol) was added, refluxed for 16 h while silica thin layer chromatography was performed (50% ethyl acetate in hexane, Rf=0.1). From the reaction mixture volatiles were removed and the residue was diluted with water (20 mL). Thereafter, the pH of this mixture was adjusted to 7 with 1N aqueous HCl. The resulting precipitate was filtered and dried. The obtained solid was triturated with ether to get 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (437) (920 mg, 87%) as a white solid.

후처리

  1. temperaturerefluxed for 16 h while silica thin layer chromatography
  2. customFrom the reaction mixture volatiles were removed
  3. additionthe residue was diluted with water (20 mL)
  4. filtrationThe resulting precipitate was filtered
  5. customdried
  6. customThe obtained solid was triturated with ether

출처 및 근거

ORD 기록
ord-d74a4fddb62b4dacbe7c2d5579154d7a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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