Acetic Acid → 4-[[N-(2-amino-5-trifluoromethoxybenzoyl)glycyl]aminomethyl]-1-(4-isopropylbenzyl)piperidine

HRID 133609

반응식

HRID 133609 반응식
C(O)(=O)C.C(OC([NH:12][C:13]1[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][C:14]=1[C:15]([NH:17][CH2:18][C:19]([NH:21][CH2:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:20])=[O:16])=O)(C)(C)C.[CH:38]([C:41]1[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][CH:42]=1)([CH3:40])[CH3:39]>CO>[NH2:12][C:13]1[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][C:14]=1[C:15]([NH:17][CH2:18][C:19]([NH:21][CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:45][C:44]2[CH:47]=[CH:48][C:41]([CH:38]([CH3:40])[CH3:39])=[CH:42][CH:43]=2)[CH2:25][CH2:24]1)=[O:20])=[O:16]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 326CuminaldehydeHCID 184262354-[{N-(2-(tert-butoxycarbonylamino)-5-trifluoromethoxybenzoyl)glycyl}aminomethyl]piperidine

생성물 1

HCID 184262264-[[N-(2-amino-5-trifluoromethoxybenzoyl)glycyl]aminomethyl]-1-(4-isopropylbenzyl)piperidine

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

Acetic acid (10 mL) was added to a mixture of 4-[[N-(2-(tert-butoxycarbonylamino)-5-(trifluoromethoxy)benzoyl)glycyl]aminomethyl]piperidine (0.050 mmol) with 4-isopropylbenzaldehyde (0.060 mmol), NaH3CN (0.15 mmol) and methanol (1.3 mL), and the resulting mixture was stirred at 60° C. for 8 hours, cooled to room temperature, then loaded onto a Varian™ SCX column and washed with methanol (10 mL). The obtained crude product was eluted with a 2 M methanol solution of NH3 (5 mL) and concentrated. A 4 M dioxane solution of HCl (2 mL) was then added to the resulting residue, and the obtained solution was stirred at room temperature overnight, concentrated and then purified by preparative TLC to provide 4-[[N-(2-amino-5-trifluoromethoxybenzoyl)glycyl]aminomethyl]-1-(4-isopropylbenzyl)piperidine (Compd. No. 1903) (6.6 mg, 26%). The purity was determined by RPLC/MS (93%). ESI/MS m/e 507 (M++H, C26H33F3N4O3).

후처리

  1. temperaturecooled to room temperature
  2. washwashed with methanol (10 mL)
  3. customThe obtained crude product
  4. washwas eluted with a 2 M methanol solution of NH3 (5 mL)
  5. concentrationconcentrated
  6. additionA 4 M dioxane solution of HCl (2 mL) was then added to the resulting residue
  7. stirringthe obtained solution was stirred at room temperature overnight
  8. concentrationconcentrated
  9. custompurified by preparative TLC

출처 및 근거

ORD 기록
ord-2c8c0fbe593d48b5877d92f63a254a24
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390830B1

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