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Formaldehyde → (R)-3-[{N-(2-amino-5-trifluoromethylbenzoyl)glycyl}amino]-1-{4-chloro-3-(dimethylamino)benzyl}pyrrolidine

HRID 1280969
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1280969
N[C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][C:38]=1[Cl:39])[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([NH:11][C:12](=[O:35])[CH2:13][NH:14][C:15](=[O:34])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=2[NH:26]C(OC(C)(C)C)=O)[CH2:7]1.[CH3:40]O.C=O.[BH3-][C:45]#[N:46].[Na+]>C(O)(=O)C>[NH2:26][C:17]1[CH:18]=[CH:19][C:20]([C:22]([F:25])([F:24])[F:23])=[CH:21][C:16]=1[C:15]([NH:14][CH2:13][C:12]([NH:11][C@@H:8]1[CH2:9][CH2:10][N:6]([CH2:5][C:4]2[CH:3]=[CH:2][C:38]([Cl:39])=[C:37]([N:46]([CH3:45])[CH3:40])[CH:36]=2)[CH2:7]1)=[O:35])=[O:34]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 69215338(R)-1-(3-amino-4-chlorobenzyl)-3-[{N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl}amino]pyrrolidine

Produkt 1

HCID 69214592(R)-3-[{N-(2-amino-5-trifluoromethylbenzoyl)glycyl}amino]-1-{4-chloro-3-(dimethylamino)benzyl}pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of (R)-1-(3-amino-4-chlorobenzyl)-3-[{N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl}amino]pyrrolidine (44.9 mg), methanol (0.95 mL), acetic acid (0.05 mL), and 37% aqueous HCHO solution (0.15 mL) was added NaBH3CN (38 mg). The reaction mixture was stirred at 50° C. overnight. The mixture was cooled to room temperature and evaporated. To the residue was added 2 N aqueous NaOH solution and ethyl acetate, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried and concentrated, and the residue was loaded onto Varian™ SCX column and washed with CH3OH. Product was eluted off using 2 N NH3 in CH3OH and concentrated. The residue was dissolved in 50% conc. HCl/dioxane and the solution was stirred at room temperature for 1 h. The reaction mixture was adjusted to pH 10 with 5 N aqueous NaOH solution and extracted with ethyl acetate (2 times). The combined extracts were dried over Na2SO4, filtered, and evaporated. Preparative TLC (SiO2, 20% MeOH/AcOEt) gave (R)-3-[{N-(2-amino-5-trifluoromethylbenzoyl)glycyl}amino]-1-{4-chloro-3-(dimethylamino)benzyl}pyrrolidine (Compound No. 2133). (10.9 mg, 28%): The purity was determined by RPLC/MS (95%); ESI/MS m/e 498.3 (M++H, C23H27ClF3N5O2).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customevaporated
  3. additionTo the residue was added 2 N aqueous NaOH solution and ethyl acetate
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. customThe combined organic layers were dried
  7. concentrationconcentrated
  8. washwashed with CH3OH
  9. washProduct was eluted off
  10. concentrationconcentrated
  11. dissolutionThe residue was dissolved in 50% conc. HCl/dioxane
  12. stirringthe solution was stirred at room temperature for 1 h
  13. extractionextracted with ethyl acetate (2 times)
  14. dry with materialThe combined extracts were dried over Na2SO4
  15. filtrationfiltered
  16. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9d5cfa8c237f413299aa4b154b37f3d2
Quelldatensatz
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06451842B1

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