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Hydrochloric Acid → HCID 86602033、化合物

HRID 2189409
ノート
印刷プレビュー

反応式

HRID 2189409 の反応式
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[C:14]([O:21][C@@H:22]3[O:48][C@H:47]([CH2:49][O:50][C:51](=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53])[C@@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C@H:31]([O:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[C@H:23]3[O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[N:15][NH:16][C:17]=2[CH:18]([CH3:20])[CH3:19])=[C:8]([CH3:57])[CH:7]=1.[CH2:58]([NH:65][CH2:66][CH2:67][C:68]([NH2:70])=[O:69])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1.[I-].[Na+].Cl>C(#N)C.C(O)C>[CH2:58]([N:65]([CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[C:14]([O:21][C@@H:22]3[O:48][C@H:47]([CH2:49][O:50][C:51](=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53])[C@@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C@H:31]([O:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[C@H:23]3[O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[N:15][NH:16][C:17]=2[CH:18]([CH3:20])[CH3:19])=[C:8]([CH3:57])[CH:7]=1)[CH2:66][CH2:67][C:68](=[O:69])[NH2:70])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 5238Sodium Iodide2 回HCID 854513-BenzylaminopropionamideHCID 689441234-{[4-(3-Chloropropoxy)-2-methylphenyl]methyl}-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazole

生成物 1

HCID 86602033HCID 86602033、化合物収率 61.7%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

A mixture of 4-{[4-(3-chloropropoxy)-2-methylphenyl]-methyl}-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (1.34 g), 3-benzylaminopropionamide (0.73 g), sodium iodide (0.24 g), ethanol (6 mL) and acetonitrile (6 mL) was stirred at 70° C. for 2 days. To the reaction mixture was added sodium iodide (0.2 g), and the mixture was further stirred at 75° C. for 24 hours. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/5−dichloromethane/methanol=15/1) to give the title compound (0.97 g).

後処理

  1. stirringthe mixture was further stirred at 75° C. for 24 hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/5−dichloromethane/methanol=15/1)

出典と根拠

ORDレコード
ord-6fdff3e5fe134ea281f50796d58b9587
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08324176B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート