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

HRID 1176794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1176794
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 (2R)-pyrrolidine-2-carboxylate hydrochloride

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-aa46ff76b34a406d8723d471002ea434
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842825B2

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