1,1'-Carbonyldiimidazole → 4-[2-(2-Carbamoyl-ethyl)-5-phenylpyrrol-1-yl]-benzoic acid tert-butyl ester

HRID 82749Notes

Reaction equation

[C:1]([O:5][C:6](=[O:29])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][CH:15]=[C:14]2[CH2:24][CH2:25][C:26](O)=[O:27])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C1N=C[N:32](C(N2C=NC=C2)=O)C=1.C([O-])(=O)C.[NH4+]>C1COCC1>[C:1]([O:5][C:6](=[O:29])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][CH:15]=[C:14]2[CH2:24][CH2:25][C:26](=[O:27])[NH2:32])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

To a stirred solution of 4-[2-(2-carboxy-ethyl)-5-phenyl-pyrrol-1yl]-benzoic acid tert-butyl ester (1.33 mmol, 1.0 eq.) in THF (10 ml) was added CDI (1,1′carbonyldiimidazole, 1.60 mmol, 1.2 eq). The mixture was stirred at 45° C. for 2 h. To the reaction mixture was then added ammonium acetate (1.72 mmol, 1.3 eq.). The mixture was stirred at 45° C. for 16 hours.

Workup

stirringThe mixture was stirred at 45° C. for 16 hours

Sources & evidence

ORD record: ord-b54dd3f4b6434ec483669f620103ecb8
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846736B2

Reaction notes

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