Toluene → HCID 86729768, compound

HRID 2272611Notes

Reaction equation

C1(C(CC)C[CH:9](C(O)=O)[C:10](O)=[O:11])C=CC=CC=1.C([O:21][C:22](=[O:24])[CH3:23])(=O)C.[C:25]1([CH3:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[NH2:32][C:33]1[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[C:35]([Cl:41])[CH:34]=1>[Cl-].[Na+].O>[Cl:41][C:35]1[CH:34]=[C:33]([NH:32][C:10](=[O:11])[CH2:9][CH:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:23][C:22]([OH:21])=[O:24])[CH:40]=[CH:39][C:36]=1[C:37]#[N:38]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 3-phenylpentanedicarboxylic acid (1.0 g, 4.80 mmol) in acetic anhydride (0.453 mL, 4.80 mmol) was stirred at 100° C. for 14 hr. The reaction mixture was concentrated, to the residue was added toluene (10 mL), and 4-amino-2-chlorobenzonitrile (0.733 g, 4.80 mmol) and TEA (0.669 mL, 4.80 mmol) were added thereto. The mixture was stirred at 80° C. for 3 hr, brine was added thereto at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane) to give 5-((3-chloro-4-cyanophenyl)amino)-5-oxo-3-phenylpentanoic acid (1.200 g, 3.50 mmol, 72.9%) as a pale-yellow powder.

Workup

concentrationThe reaction mixture was concentrated, to the residue
additionwere added
extractionat room temperature, and the mixture was extracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
customdried
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-4c2e215574734ac98cc42a90292cb3c5
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120776B2

Reaction notes

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