Methanol → Methyl (2S,4EZ)-4-(methoxyimino)-1-{[2'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]carbonyl}-2-pyrrolidinecarboxylate

HRID 457932

Reaction equation

HRID 457932 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][C@H:9]1[C:16]([OH:18])=[O:17])=[O:7])(C)(C)C.[F:19][C:20]([F:37])([F:36])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:32]=[CH:31][C:30](C(O)=O)=[CH:29][CH:28]=1.[CH3:38]O>>[CH3:15][O:14][N:13]=[C:11]1[CH2:12][N:8]([C:6]([C:30]2[CH:29]=[CH:28][C:27]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[C:20]([F:19])([F:36])[F:37])=[CH:32][CH:31]=2)=[O:7])[C@H:9]([C:16]([O:18][CH3:38])=[O:17])[CH2:10]1

Participants

4

Reactant 3

HCID 887MethanolHCID 27827142'-Trifluoromethyl (1,1'-biphenyl)-4-carboxylic acidHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131726292Methyl (2S,4EZ)-4-(methoxyimino)-1-{[2'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]carbonyl}-2-pyrrolidinecarboxylate

Procedure

Following the general method as outlined in Example 11, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, 2′-(trifluoromethyl)[1,1′-biphenyl]-4-carboxylic acid, and methanol, the title compound was isolated as a mixture of two isomers in 86.3% purity by HPLC.

Sources & evidence

ORD record
ord-945aee578b904e09903dc6b30a78fbb3
Source dataset
uspto-grants-2007_03
Patent number
US07189754B2

Linked notes

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