1,4-Dioxane → (S)-3-amino-2-(4-chlorophenyl)propanoic acid hydrochloride

HRID 1675867ノート

反応式

HRID 1675867 の反応式
Cl.O1CCOCC1.C(OC([NH:15][CH2:16][C@H:17]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[C:18]([OH:20])=[O:19])=O)(C)(C)C.O1CCOCC1>C(Cl)Cl>[ClH:27].[NH2:15][CH2:16][C@H:17]([C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)[C:18]([OH:20])=[O:19]

参加物

5

反応物 3

HCID 312751,4-DioxaneHCID 204431481,4-Dioxane hydrochlorideHCID 29947824HCID 29947824、化合物

生成物 1

HCID 66617945(S)-3-amino-2-(4-chlorophenyl)propanoic acid hydrochloride収率 153.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4M HCl/dioxane (5.49 mL, 22.0 mmol) was added to a solution of (S)-3-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)propanoic acid (0.329 g, 1.10 mmol) in 2:1 dioxane:DCM (10 mL). The reaction mixture was stirred at room temperature overnight (16 hours), after which it was concentrated to ⅓ volume. The resulting cloudy mixture was diluted with ether, and the mixture was concentrated again to ⅓ volume. The mixture was diluted again with ether (20 mL), and the solids were isolated by filtration through a medium frit funnel with nitrogen pressure. The solids were rinsed with ether (5×10 mL), dried under nitrogen pressure, and dried in vacuo to give (S)-3-amino-2-(4-chlorophenyl)propanoic acid hydrochloride (0.199 g, 76.8% yield) as a white powder. HPLC>99 area % pure. LC/MS (APCI+) m/z 200.

後処理

  1. concentrationafter which it was concentrated
  2. additionThe resulting cloudy mixture was diluted with ether
  3. concentrationthe mixture was concentrated again
  4. additionThe mixture was diluted again with ether (20 mL)
  5. customthe solids were isolated by filtration through a medium frit funnel with nitrogen pressure
  6. washThe solids were rinsed with ether (5×10 mL)
  7. customdried under nitrogen pressure
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-cda1c5c33af646fd822aae4be9bfc829
出典データセット
uspto-grants-2011_08
特許番号
US08003651B2

反応ノート

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