Reaktion #507239

ord-79c600872cb440bf9f7ccd47ee5a16ff

Reaktionsgleichung

C=C[C@@H]1C[C@]1(NC(=O)n1cc[n+](C)c1)C(=O)OCC.[I-]
compounds 34
C=C[C@@H]1C[C@]1(NC(=O)n1cc[n+](C)c1)C(=O)OCC.[I-]
1-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropyl-carbamoyl)-3-methyl-1H-imidazol-3-ium iodide
C=CCCCCCN(C)C(=O)[C@@H]1C[C@@H](O)CN1
71a
C=CCCCCCN(C)C(=O)[C@@H]1C[C@@H](O)CN1
(2S,4R)-2-N-(hept-6-enyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamide
C=CCCCCN(C)C(=O)[C@@H]1C[C@@H](O)CN1C(=O)N[C@]1(C(=O)OCC)C[C@@H]1C=C
compound 50
C=CCCCCN(C)C(=O)[C@@H]1C[C@@H](O)CN1C(=O)N[C@]1(C(=O)OCC)C[C@@H]1C=C
(1R)-1-{[2(S)-(hex-5-enyl-methyl-carbamoyl)-4(R)-hydroxy-pyrrolidine-N-carbonyl]amino}-2(R)-vinyl-cyclopropanecarboxylic acid ethyl ester
→
C=C[C@H]1C[C@]1(NC(=O)N1C[C@H](O)C[C@H]1C(=O)N(C)CCCCC=CC)C(=O)OCC
Compound 72a
Ausbeute 38.0%
C=C[C@H]1C[C@]1(NC(=O)N1C[C@H](O)C[C@H]1C(=O)N(C)CCCCC=CC)C(=O)OCC
(1R)-1-{[2(S)-(hept-5-enyl-methyl-carbamoyl)-4(R)-hydroxy-pyrrolidine-N-carbonyl]amino}-2(R)-vinyl-cyclopropanecarboxylic acid ethyl ester
Ausbeute 38.0%

Edukte

C=C[C@@H]1C[C@]1(NC(=O)n1cc[n+](C)c1)C(=O)OCC.[I-]
compounds 34
C=C[C@@H]1C[C@]1(NC(=O)n1cc[n+](C)c1)C(=O)OCC.[I-]
1-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropyl-carbamoyl)-3-methyl-1H-imidazol-3-ium iodide
C=CCCCCCN(C)C(=O)[C@@H]1C[C@@H](O)CN1
71a
C=CCCCCCN(C)C(=O)[C@@H]1C[C@@H](O)CN1
(2S,4R)-2-N-(hept-6-enyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamide
C=CCCCCN(C)C(=O)[C@@H]1C[C@@H](O)CN1C(=O)N[C@]1(C(=O)OCC)C[C@@H]1C=C
compound 50
C=CCCCCN(C)C(=O)[C@@H]1C[C@@H](O)CN1C(=O)N[C@]1(C(=O)OCC)C[C@@H]1C=C
(1R)-1-{[2(S)-(hex-5-enyl-methyl-carbamoyl)-4(R)-hydroxy-pyrrolidine-N-carbonyl]amino}-2(R)-vinyl-cyclopropanecarboxylic acid ethyl ester

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Compound 72a was synthesized from compounds 34 and 71a as a beige solid in 38% yield, following the procedure as described for compound 50.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08093379B2uspto-grants-2012_01