Triethylamine → 1-(1,2,3,4-tetrahydronaphthalen-2-ylacetyl)-L-proline methyl ester

HRID 1086267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1086267
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[CH2:11][C:12]([OH:14])=O.CCN=C=NCCCN(C)C.Cl.Cl.[CH3:28][O:29][C:30](=[O:36])[C@@H:31]1[CH2:35][CH2:34][CH2:33][NH:32]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:28][O:29][C:30](=[O:36])[C@@H:31]1[CH2:35][CH2:34][CH2:33][N:32]1[C:12](=[O:14])[CH2:11][CH:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733200methyl L-prolinate hydrochlorideHCID 100127392-(1,2,3,4-Tetrahydronaphthalen-2-yl)acetic acid

Produkt 1

HCID 537814601-(1,2,3,4-tetrahydronaphthalen-2-ylacetyl)-L-proline methyl esterAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3.4 g of 1,2,3,4-tetrahydronaphthalen-2-ylacetic acid in 50 ml of methylene chloride was added 14.1 g of WSC.HCl with stirring at room temperature. Then, 3.6 g of L-proline methyl ester hydrochloride and 2.2 g of triethylamine were added to the solution. The mixture was stirred for 17 hours at room temperature. The reaction mixture was washed with water, diluted hydrochloric acid, and saturated sodium hydrogen carbonate in this order. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 3.6 g of 1-(1,2,3,4-tetrahydronaphthalen-2-ylacetyl)-L-proline methyl ester as a colorless oil.

Aufarbeitung

  1. stirringThe mixture was stirred for 17 hours at room temperature
  2. washThe reaction mixture was washed with water, diluted hydrochloric acid, and saturated sodium hydrogen carbonate in this order
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cd39a0a7ae1448f895222c2fedae1674
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05028604

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