4-Phenylbenzoyl chloride → HCID 58714504, compound

HRID 1242558Notes

Reaction equation

HRID 1242558 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.[NH2:19][C:20](=[N:34]O)[CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.[C:36]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:41]=[CH:40][C:39](C(Cl)=O)=[CH:38][CH:37]=1>>[C:36]1([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:41]=[CH:40][C:39]([C:6]([N:8]2[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][C@H:9]2[C:16]2[O:18][N:34]=[C:20]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]3)[N:19]=2)=[O:7])=[CH:38][CH:37]=1

Participants

4

Reactant 3

HCID 841514-Phenylbenzoyl chlorideHCID 54001703HCID 54001703, compound2×HCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid2×

Product 1

HCID 58714504HCID 58714504, compoundYield 60%

Procedure

Following the general methods as outlined in Example 1 (Method A), starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidine-carboxylic acid (intermediate 2), tert-butyl 4-[amino(hydroxyimino)methyl]-1-piperidinecarboxylate (Intermediate 7) and [1,1′-biphenyl]-4-carbonyl chloride, the desired compound, tert-butyl 4-{5-[(2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-4-(methoxyimino)pyrrolidinyl]-1,2,4-oxadiazol-3-yl}-1-piperidinecarboxylate, was isolated, after flash-chromatography (cyclohexane/ethylacetate 6/4), as a mixture of E-/Z-isomers in 60% yield (97.9% purity by HPLC).

Sources & evidence

ORD record
ord-8fa25d14dbd44dc9b303c0a2ed646431
Source dataset
uspto-grants-2006_10
Patent number
US07115639B2

Reaction notes

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