Hydrochloric Acid → HCID 178457444、化合物

HRID 2169469ノート

反応式

HRID 2169469 の反応式
[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]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178457480HCID 178457480、化合物

生成物 1

HCID 178457444HCID 178457444、化合物収率 82.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-25b39e5760cd4da0a617b303410cce39
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

読み込み中…