Hydrochloric Acid → HCID 178457444, 화합물

HRID 2169469노트

반응식

HRID 2169469 반응식
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:41]([CH3:43])[CH3:42])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.Cl.C([O-])(O)=O.[Na+]>O1CCCC1.O>[OH:8][CH2:9][CH2:10][N:11]([CH:41]([CH3:43])[CH3:42])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178457480HCID 178457480, 화합물

생성물 1

HCID 178457444HCID 178457444, 화합물수율 82.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylicacid[2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (438) (150 mg, 0.248 mmol) of in tetrahydrofuran (4 mL), was added 1N HCl (1 mL), then this reaction mixture was stirred for 1 h, at room temperature, After completion of the reaction, volatile substances were removed the from the reaction, then dilute with water (10 mL) and adjust with NaHCO3 to pH8, then extract with ethyl acetate (2×30 mL), then organic part was dried over sodium sulfate, then concentrated, resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography using 50-60% ethyl acetate in hexane as gradient polarity mobile phase to get 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylicacid (2-hydroxyethyl)-isopropylamide (439) (100 mg, 82%) as white sticky liquid.

후처리

  1. customAfter completion of the reaction, volatile substances
  2. customwere removed the
  3. customfrom the reaction
  4. extractionextract with ethyl acetate (2×30 mL)
  5. dry with materialorganic part was dried over sodium sulfate
  6. concentrationconcentrated
  7. customresulting crude product
  8. customwas purified by normal silica gel (100-200 mesh) column chromatography

출처 및 근거

ORD 기록
ord-25b39e5760cd4da0a617b303410cce39
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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