4-(Pyrimidin-5-yl)benzoic acid → Methyl (2S,4EZ)-4-(methoxyimino)-1-[4-(5-pyrimidinyl)benzoyl]-2-pyrrolidinecarboxylate

HRID 457925Notes

Reaction equation

HRID 457925 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.[N:20]1[CH:25]=[C:24]([C:26]2[CH:34]=[CH:33][C:29](C(O)=O)=[CH:28][CH:27]=2)[CH:23]=[N:22][CH:21]=1>>[CH3:1][O:2][N:3]=[C:4]1[CH2:8][N:7]([C:9](=[O:11])[C:29]2[CH:28]=[CH:27][C:26]([C:24]3[CH:25]=[N:20][CH:21]=[N:22][CH:23]=3)=[CH:34][CH:33]=2)[C@H:6]([C:16]([O:18][CH3:19])=[O:17])[CH2:5]1

Participants

3

Reactant 2

HCID 41872474-(Pyrimidin-5-yl)benzoic acidHCID 585854781-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate

Product 1

HCID 131726286Methyl (2S,4EZ)-4-(methoxyimino)-1-[4-(5-pyrimidinyl)benzoyl]-2-pyrrolidinecarboxylateYield 68%

Procedure

Following the general methods as outlined in Example 4, starting from 1-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate and 4-(5-pyrimidinyl)benzoic acid, the title compound was obtained, after flash-chromatography, as a mixture of two isomers as an oil in 68% yield (93.0% purity by HPLC).

Sources & evidence

ORD record
ord-56442d9ec96e4ba293d62f7636dffbae
Source dataset
uspto-grants-2007_03
Patent number
US07189754B2

Reaction notes

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