N-Hydroxyacetamidine → (3Ez,5s)-5-(3-methyl-1,2,4-oxadiazol-5-yl)-1-{[2'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]carbonyl}-3-pyrrolidinone o-methyloxime

HRID 1242557Notes

Reaction equation

HRID 1242557 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)=[O:7])(C)(C)C.[C:19](=[N:22]O)([NH2:21])[CH3:20].[F:24][C:25]([F:42])([F:41])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]1[CH:37]=[CH:36][C:35](C(O)=O)=[CH:34][CH:33]=1>>[CH3:15][O:14][N:13]=[C:11]1[CH2:10][C@@H:9]([C:16]2[O:18][N:22]=[C:19]([CH3:20])[N:21]=2)[N:8]([C:6]([C:35]2[CH:34]=[CH:33][C:32]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[C:25]([F:24])([F:41])[F:42])=[CH:37][CH:36]=2)=[O:7])[CH2:12]1

Participants

4

Reactant 3

HCID 30926N-Hydroxyacetamidine2×HCID 27827142'-Trifluoromethyl (1,1'-biphenyl)-4-carboxylic acid2×HCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid2×

Product 1

HCID 58714561(3Ez,5s)-5-(3-methyl-1,2,4-oxadiazol-5-yl)-1-{[2'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]carbonyl}-3-pyrrolidinone o-methyloximeYield 44%

Procedure

Following the general methods as outlined in Example 1 (Method B), starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidine-carboxylic acid (Intermediate 2), N′-hydroxyethanimidamide (Intermediate 7) and 2′-(trifluoromethyl) [1,1′-biphenyl]-4-carboxylic acid (Intermediate 10), the title compound was isolated, after flash-chromatography, as a mixture of E-/Z-isomers as an oil in 44% yield (88.2% purity by HPLC).

Sources & evidence

ORD record
ord-6674888fc3324ef6881877c90404cee4
Source dataset
uspto-grants-2006_10
Patent number
US07115639B2

Reaction notes

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