(1R)-1-{[2(S)-(hex-5-enyl-methyl-carbamoyl)-4(R)-hydroxy-pyrrolidine-N-carbonyl]amino}-2(R)-vinyl-cyclopropanecarboxylic acid ethyl ester → (1R)-1-{[2(S)-(hept-5-enyl-methyl-carbamoyl)-4(R)-hydroxy-pyrrolidine-N-carbonyl]amino}-2(R)-vinyl-cyclopropanecarboxylic acid ethyl ester
Reaction equation
[I-].[CH2:2]([O:4][C:5]([C@@:7]1([NH:12][C:13](N2C=C[N+](C)=C2)=[O:14])[CH2:9][C@H:8]1[CH:10]=[CH2:11])=[O:6])[CH3:3].[CH2:21]([N:28]([CH3:37])[C:29]([C@@H:31]1[CH2:35][C@@H:34]([OH:36])[CH2:33][NH:32]1)=[O:30])[CH2:22][CH2:23][CH2:24][CH2:25][CH:26]=[CH2:27].C(OC([C@@]1(NC(N2C[C@H](O)C[C@H]2C(=O)N(CCCCC=C)C)=O)C[C@@H]1C=C)=O)C>>[CH2:2]([O:4][C:5]([C@@:7]1([NH:12][C:13]([N:32]2[CH2:33][C@H:34]([OH:36])[CH2:35][C@H:31]2[C:29](=[O:30])[N:28]([CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH:26][CH3:27])[CH3:37])=[O:14])[CH2:9][C@@H:8]1[CH:10]=[CH2:11])=[O:6])[CH3:3]Participants
4
Reactant 3
Product 1
Procedure
Compound 72a was synthesized from compounds 34 and 71a as a beige solid in 38% yield, following the procedure as described for compound 50.
Sources & evidence
- ORD record
- ord-fd88f99970964b598fcd681c452239a9
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003659B2
Reaction notes
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