HCID 178450806, 화합물 → HCID 178524866, 화합물

HRID 2169314노트

반응식

HRID 2169314 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][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

참가 물질

3

반응물 1

HCID 178450806HCID 178450806, 화합물

생성물 1

HCID 178524866HCID 178524866, 화합물수율 55.44%

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e544742fce6c47179f410d7d7c59ea15
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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