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Citric Acid → HCID 90060183、化合物

HRID 1779155
ノート
印刷プレビュー

反応式

HRID 1779155 の反応式
C([Si](C)(C)[O:6][CH2:7][CH2:8][C@:9]([OH:58])([C@@H:17]([C:38](=[O:57])[NH:39][C@H:40]([C:53]([O:55][CH3:56])=[O:54])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]#[C:51][CH3:52])=[CH:44][CH:43]=1)/[CH:18]=[CH:19]/[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])OCC[O:27]1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(C)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[Cl-].[Na+].O>C(#N)C>[CH2:49]([O:48][C:45]1[CH:44]=[CH:43][C:42]([CH2:41][C@H:40]([NH:39][C:38]([C@@H:17](/[CH:18]=[CH:19]/[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26](=[O:27])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C@@:9]([OH:58])([CH2:8][CH2:7][OH:6])[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[O:57])[C:53]([O:55][CH3:56])=[O:54])=[CH:47][CH:46]=1)[C:50]#[C:51][CH3:52]
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

6

反応物 4

HCID 311Citric AcidHCID 962WaterHCID 5234Sodium ChlorideHCID 123758623HCID 123758623、化合物

生成物 1

HCID 90060183HCID 90060183、化合物収率 57%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

No. 5327507 Compound C (50.8 g, 59.2 mmol) was dissolved in acetonitrile (560 mL), and then an aqueous solution of 0.5 M citric acid (249 mL, 125 mmol) was added to the solution, which was stirred at 60° C. for 2.5 hours. After confirming that inner temperature had returned to room temperature, a mixture of a saturated aqueous solution of sodium chloride (51 mL) and water (813 mL) was added. The solution was extracted with 20% ethyl acetate/n-hexane (457 mL) 3 times. The organic layers were combined, then washed twice with a saturated aqueous solution (230 mL) of sodium chloride, dried over anhydrous sodium sulfate, and filtered. The solvent was then distilled off under reduced pressure and the residue was purified on Biotage (silica gel, n-hexane/acetone) to obtain 23.6 g (33.7 mmol, 57% yield) of No. 5217614 (Compound D).

後処理

  1. customhad returned to room temperature
  2. additionwas added
  3. extractionThe solution was extracted with 20% ethyl acetate/n-hexane (457 mL) 3 times
  4. washwashed twice with a saturated aqueous solution (230 mL) of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customthe residue was purified on Biotage (silica gel, n-hexane/acetone)
  9. customto obtain 23.6 g (33.7 mmol, 57% yield) of No

出典と根拠

ORDレコード
ord-94dc608ce1ab4bcab559c6a35a8593fa
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09266853B2

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