Diisopropylethylamine → tert-Butyl (1R,3S,4S,6R)-3-{[(2S)-2-aminocarbonyl-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate

HRID 456777

Reaktionsgleichung

Reaktionsgleichung von HRID 456777
[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14]([OH:16])=O)[C@H:12]2[CH2:17][C@@H:9]1[C@H:10]([OH:18])[CH2:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[C:24]([NH2:26])=[O:25].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl.O>[NH2:26][C:24]([C@@H:20]1[CH2:21][CH2:22][CH2:23][N:19]1[C:14]([C@@H:13]1[C@H:12]2[CH2:17][C@H:9]([C@H:10]([OH:18])[CH2:11]2)[N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:16])=[O:25]

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 111306L-ProlinamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69133789(1R,3S,4S,6R)-2-(tert-Butoxycarbonyl)-6-hydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylic Acid

Produkt 1

HCID 86598928tert-Butyl (1R,3S,4S,6R)-3-{[(2S)-2-aminocarbonyl-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylateAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a suspension of (1R,3S,4S,6R)-2-(tert-butoxycarbonyl)-6-hydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylic acid obtained in Example 42-6 (45 g) in chloroform (450 mL), were added (2S)-2-pyrrolidinecarboxamide (21 g), 1-hydroxybenzotriazole hydrate (29.5 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (36.9 g) and diisopropylethylamine (45.3 g) in water bath. The mixture was stirred at room temperature for 5 hrs. The precipitate collected by vacuum filtration and washed with ethyl acetate to give the target compound as a solid (51.5 g).

Aufarbeitung

  1. filtrationThe precipitate collected by vacuum filtration
  2. washwashed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-aba9c70e279c4a41adb2c84d7a3160fd
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186731B2

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