Ethyl Acetate → HCID 178524873、化合物

HRID 2169467ノート

反応式

HRID 2169467 の反応式
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

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 178450813HCID 178450813、化合物

生成物 1

HCID 178524873HCID 178524873、化合物収率 87.3%

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 21881883Oxolane--water (1/1)溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d74a4fddb62b4dacbe7c2d5579154d7a
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

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