HCID 178450806、化合物 → HCID 178524866、化合物

HRID 2169314ノート

反応式

HRID 2169314 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][CH:30]=3)[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:9]=1)=[O:7])(C)(C)C>O1CCCC1.O>[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][CH: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

3

反応物 1

HCID 178450806HCID 178450806、化合物

生成物 1

HCID 178524866HCID 178524866、化合物収率 55.44%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (282) (1.6 g. 3.48 mmol) in a mixture of tetrahydrofuran:water (2:1) (90 mL), was added lithium-hydroxide monohydrate (2.9 g, 69.57 mmol) and the reaction mixture was refluxed for 18 h. After completion of the reaction, all volatiles were evaporated, added water (30 mL) and washed with ethyl acetate (2×20 mL) to remove non acidic impurities. The separated aqueous part was acidified with 1N HCl to reach a pH of about 5 to 6. The acidified aqueous part was extracted with ethyl acetate (4×50 mL), dried and concentrated to get 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (283) (780 mg, 55.44%) as a white solid.

後処理

  1. additionwas added lithium-hydroxide monohydrate (2.9 g, 69.57 mmol)
  2. temperaturethe reaction mixture was refluxed for 18 h
  3. customAfter completion of the reaction
  4. customall volatiles were evaporated
  5. additionadded water (30 mL)
  6. washwashed with ethyl acetate (2×20 mL)
  7. customto remove non acidic impurities
  8. extractionThe acidified aqueous part was extracted with ethyl acetate (4×50 mL)
  9. customdried
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-e544742fce6c47179f410d7d7c59ea15
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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