4-(4-Fluorophenyl)benzoic acid → Methyl (2S,4EZ)-1-[(4'-fluoro[1,1'-biphenyl]4-yl)carbonyl]-4-(methoxyimino)-2-pyrrolidinecarboxylate

HRID 457924Notes

Reaction equation

HRID 457924 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[CH2:8][N:7]([C:9]([O:11]C(C)(C)C)=O)[C@H:6]([C:16]([O:18][CH3:19])=[O:17])[CH2:5]1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30](C(O)=O)=[CH:29][CH:28]=2)=[CH:23][CH:22]=1>>[F:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:9]([N:7]3[CH2:8][C:4](=[N:3][O:2][CH3:1])[CH2:5][C@H:6]3[C:16]([O:18][CH3:19])=[O:17])=[O:11])=[CH:29][CH:28]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 27826894-(4-Fluorophenyl)benzoic acidHCID 585854781-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate

Product 1

HCID 131726285Methyl (2S,4EZ)-1-[(4'-fluoro[1,1'-biphenyl]4-yl)carbonyl]-4-(methoxyimino)-2-pyrrolidinecarboxylateYield 39%

Procedure

Following the general methods as outlined in Example 4, starting 1-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate and 4′-fluoro[1,1′-biphenyl]-4-carboxylic acid, the title compound was isolated, after flash-chromatography, as a mixture of two isomers as an oil in 39% yield (97.6% purity by HPLC).

Sources & evidence

ORD record
ord-8a016a80717a4eae9b8aba91357f6c54
Source dataset
uspto-grants-2007_03
Patent number
US07189754B2

Reaction notes

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