Trifluoroacetic acid → 2-(2-(4-(4-(Hydroxycarbonylmethoxy)phenoxy)phenyl)-acetylamino)benzoic acid methyl ester

HRID 480268Notes

Reaction equation

C(O)(C(F)(F)F)=O.[CH3:8][O:9][C:10](=[O:43])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18](=[O:42])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1>>[CH3:8][O:9][C:10](=[O:43])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18](=[O:42])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][C:35]([OH:37])=[O:36])=[CH:31][CH:32]=2)=[CH:22][CH:21]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid2×

HCID 697468002-(2-(4-(4-(t-Butoxycarbonylmethoxy)-phenoxy)phenyl)acetylamino)benzoic acid methyl ester

Product 1

HCID 207810352-(2-(4-(4-(Hydroxycarbonylmethoxy)phenoxy)phenyl)-acetylamino)benzoic acid methyl esterYield 100%

Procedure

TFA (4 ml) was added to 2-(2-(4-(4-(t-butoxycarbonylmethoxy)-phenoxy)phenyl)acetylamino)benzoic acid methyl ester produced by the Example 27 and the mixture was stirred for 2 hours at room temperature. After the reaction, TFA was distilled out under reduced pressure and the product was dissolved in ethyl acetate. The organic layer was washed with water and dried with anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to quantitatively obtain the subject compound (164 mg). The result of 1H-NMR was consistent with the above structure.

Workup

customproduced by the Example 27
distillationwas distilled out under reduced pressure
dissolutionthe product was dissolved in ethyl acetate
washThe organic layer was washed with water
dry with materialdried with anhydrous magnesium sulfate
distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record: ord-6d4de1891e7e44d88d1da27fb68f6874
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06649656B1

Reaction notes

Loading…