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

HRID 133609

Reaktionsgleichung

Reaktionsgleichung von HRID 133609
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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2c8c0fbe593d48b5877d92f63a254a24
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390830B1

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