Water → methyl N-benzyloxy-carbonyl-L-prolyl-1-aminocyclopentane-1-carboxylate

HRID 64776

Reaktionsgleichung

Reaktionsgleichung von HRID 64776
[CH2:1]([N:3](CC)[CH2:4][CH3:5])[CH3:2].[CH2:8]([O:15]C(N1CCC[C@H]1C(O)=O)=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH2:26][C:27]1([C:32]([O:34][CH3:35])=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28]1.[OH2:36].[O:37]1[CH2:42][CH2:41]OCC1>C(OCC)(=O)C>[CH2:8]([O:15][N:3]1[CH2:4][CH2:5][C:41](=[C:42]=[O:37])[C@H:1]1[C:2]([CH:28]1[CH2:29][CH2:30][CH2:31][C:27]1([NH2:26])[C:32]([O:34][CH3:35])=[O:33])=[O:36])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

7

Edukt 5

HCID 962WaterHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 101987Benzyloxycarbonyl-L-prolineHCID 231225Methyl 1-amino-1-cyclopentanecarboxylate (H-Ac5c-OMe)

Produkt 1

HCID 86740982methyl N-benzyloxy-carbonyl-L-prolyl-1-aminocyclopentane-1-carboxylateAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5.4 ml of triethylamine and 13.5 g of the N-hydroxysuccinimide ester of N-benzyloxycarbonyl-L-proline were added to 5.6 g of methyl 1-aminocyclopentane-1-carboxylate in 50 ml of dioxane at 10° C., the reaction mixture was stirred for 2 hours at this temperature, 20 ml of water were then added and the reaction was allowed to continue for 20 hours at room temperature. The mixture was taken up in ethyl acetate, and the organic phase was washed successively with 10% strength aqueous citric acid solution, sodium carbonate solution and water, dried over sodium sulfate and evaporated down under reduced pressure. Crystallization of the solid residue gave 11.5 g (79%) of methyl N-benzyloxy-carbonyl-L-prolyl-1-aminocyclopentane-1-carboxylate.

Aufarbeitung

  1. additionwere then added
  2. washthe organic phase was washed successively with 10% strength aqueous citric acid solution, sodium carbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. customevaporated down under reduced pressure
  5. customCrystallization of the solid residue

Quellen und Nachweise

ORD-Eintrag
ord-370cbb45113842a6869250f03197467e
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04610817

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