Hydrochloric Acid → HCID 178519975、化合物

HRID 2169477ノート

反応式

HRID 2169477 の反応式
[Si]([O:8][CH2:9][CH2:10][N:11]([CH2:41][CH:42]1[CH2:44][CH2:43]1)[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>[CH:42]1([CH2:41][N:11]([CH2:10][CH2:9][OH:8])[C:12]([C:14]2[C:19]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]3([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:15]=2)=[O:13])[CH2:44][CH2:43]1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 178455250HCID 178455250、化合物

生成物 1

HCID 178519975HCID 178519975、化合物収率 75.3%

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-carboxylicacid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropylmethyl-amide (446) (200 mg, 0.325 mmol) of in tetrahydrofuran (10 mL) was added (1N) aqueous HCl (2 mL). The mixture was stirred for 1 h at room temperature. After completion of the reaction, volatiles were removed, the residue diluted with water (10 mL) and pH was adjusted to 8 using NaHCO3. The mixture was extracted with ethyl acetate (2×30 mL), and the organic part was 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 gradient polarity mobile phase to get 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid cyclopropylmethyl-(2-hydroxyethyl)-amide (447) (123 mg, 75%) as a colorless gummy liquid.

後処理

  1. customAfter completion of the reaction, volatiles
  2. customwere removed
  3. additionthe residue diluted with water (10 mL) and pH
  4. extractionThe mixture was extracted with ethyl acetate (2×30 mL)
  5. customthe organic part was 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-b41f40deaecd4ad3a9123eff218ca3cd
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…