Hydrochloric Acid → 1-{2-Chloro-5-[(R)-1-(4-chloro-3,5-dimethyl-phenyl)-propylamino]-benzyl}-azetidine-3-carboxylic acid

HRID 1629749노트

반응식

HRID 1629749 반응식
C([O:5][C:6]([CH:8]1[CH2:11][N:10]([CH2:12][C:13]2[CH:18]=[C:17]([NH:19][C@@H:20]([C:23]3[CH:28]=[C:27]([CH3:29])[C:26]([Cl:30])=[C:25]([CH3:31])[CH:24]=3)[CH2:21][CH3:22])[CH:16]=[CH:15][C:14]=2[Cl:32])[CH2:9]1)=[O:7])(C)(C)C.Cl>C(Cl)Cl>[Cl:32][C:14]1[CH:15]=[CH:16][C:17]([NH:19][C@@H:20]([C:23]2[CH:28]=[C:27]([CH3:29])[C:26]([Cl:30])=[C:25]([CH3:31])[CH:24]=2)[CH2:21][CH3:22])=[CH:18][C:13]=1[CH2:12][N:10]1[CH2:9][CH:8]([C:6]([OH:7])=[O:5])[CH2:11]1

참가 물질

4

반응물 2

HCID 313Hydrochloric Acid2회HCID 673461981-{2-Chloro-5-[(R)-1-(4-chloro-3,5-dimethyl-phenyl)-propylamino]-benzyl}-azetidine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 533395461-{2-Chloro-5-[(R)-1-(4-chloro-3,5-dimethyl-phenyl)-propylamino]-benzyl}-azetidine-3-carboxylic acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of INT 58 (206 mg, 0.431 mmol) in CH2Cl2 (5 mL) was treated with HCl (4 M in dioxane, 0.43 mL, 1.726 mmol) and stirred at room temperature overnight. The mixture contained some starting material, so another portion of HCl (4 M in dioxane, 0.50 ml, 2.00 mmol) was added and stirring continued for 4 hours. Excess of HCl gas was removed by a stream of argon. The mixture was neutralized with 10% sodium bicarbonate solution then treated with 10% ammonium chloride solution and extracted first with CH2Cl2 then with EtOAc. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The title compound was purified by preparative UPLC (H2O/CH3CN).

후처리

  1. stirringstirring
  2. waitcontinued for 4 hours
  3. customExcess of HCl gas was removed by a stream of argon
  4. additionthen treated with 10% ammonium chloride solution
  5. extractionextracted first with CH2Cl2
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe title compound was purified by preparative UPLC (H2O/CH3CN)

출처 및 근거

ORD 기록
ord-b4d472d77a394a3093326a0ebdecb420
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791100B2

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