1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → tert-butyl L-prolinate

HRID 643812

Reaktionsgleichung

Reaktionsgleichung von HRID 643812
C1(C2C=CC=CC=2)C=CC(OCC2OC(C(O)=O)=CC=2)=CC=1.Cl.[C:24]([O:28][C:29](=[O:35])[C@H:30]1[CH2:34][CH2:33][CH2:32][NH:31]1)([CH3:27])([CH3:26])[CH3:25].Cl.C(N=C=NCCCN(C)C)C>O1CCCC1>[C:24]([O:28][C:29]([CH:30]1[CH2:34][CH2:33][CH2:32][NH:31]1)=[O:35])([CH3:27])([CH3:25])[CH3:26]

Komponenten

5

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 46831535-[(4-Phenylphenoxy)methyl]furan-2-carboxylic acid2×HCID 44629909tert-Butyl D-prolinate--hydrogen chloride (1/1)

Produkt 1

HCID 102884tert-butyl L-prolinateAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 5-(biphenyl-4-yloxymethyl)-furan-2-carboxylic acid (of Intermediate 8; 0.134 g, 0.46 mmol), D-proline tert-butyl ester hydrochloride (Bachem; 0.22 g, 1.1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (Avocado; 0.18 g, 0.95 mmol), and N,N-dimethylaminopyridine (0.166 g, 1.36 mmol) in tetrahydrofuran (10 mL) was stirred at room temperature for 16 h. The solvents were evaporated under reduced pressure, and water and ethyl acetate were added. The aqueous phase was extracted three times with ethyl acetate, and the combined organic layers were dried (sodium sulfate), filtered, evaporated, and purified using a Biotage Flash 40 purification system, eluting with methylene chloride/acetone 9:1, to give 5-(biphenyl-4-yloxymethyl)-furan-2-carbonyl]-D-pyrrolidine-2-carboxylic acid tert-butyl ester as a white solid (0.115 g, 56%).

Aufarbeitung

  1. customThe solvents were evaporated under reduced pressure, and water and ethyl acetate
  2. additionwere added
  3. extractionThe aqueous phase was extracted three times with ethyl acetate
  4. dry with materialthe combined organic layers were dried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. custompurified
  8. customa Biotage Flash 40 purification system
  9. washeluting with methylene chloride/acetone 9:1

Quellen und Nachweise

ORD-Eintrag
ord-4b55ed77f1a04cefaed8fcc07fbb4178
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700632B2

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