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

HRID 559409노트

반응식

HRID 559409 반응식
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]

참가 물질

5

반응물 3

HCID 312751,4-DioxaneHCID 204431481,4-Dioxane hydrochlorideHCID 29947824HCID 29947824, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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, 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.

후처리

  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. washrinsed with ether (5×10 mL)
  7. customdried under nitrogen pressure
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-b092d99ef66648bab8d3b8a0a0959bd6
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063050B2

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