Hydrochloric Acid → HCID 178484640、化合物

HRID 2169473ノート

反応式

HRID 2169473 の反応式
[Si]([O:8][CH2:9][CH2:10][N:11]([CH3:41])[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>O1CCCC1>[OH:8][CH2:9][CH2:10][N:11]([CH3:41])[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

4

反応物 2

HCID 313Hydrochloric AcidHCID 178484771HCID 178484771、化合物

生成物 1

HCID 178484640HCID 178484640、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amide (442) (180 mg, 0.313 mmol) of in tetrahydrofuran (10 mL), was added 1N HCl (2 mL), then this reaction mixture was stirred for 1 h, at room temperature, After completion of the reaction, volatiles were removed from the reaction mixture and the residue was diluted with water (10 mL) and pH was adjusted with NaHCO3 to 8. The quenched mass was extracted with ethyl acetate (2×50 mL). The combined extracts were dried and concentrated. The resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography using 50-60% ethyl acetate in hexane as a gradient polarity mobile phase to get 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-methyl-amide (443).

後処理

  1. customAfter completion of the reaction, volatiles
  2. customwere removed from the reaction mixture
  3. additionthe residue was diluted with water (10 mL) and pH
  4. extractionThe quenched mass was extracted with ethyl acetate (2×50 mL)
  5. customThe combined extracts were dried
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography

出典と根拠

ORDレコード
ord-13b1239c159b4417a64f9c12a3c3758c
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…