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

HRID 2181170Notes

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-75a54f66b71f411aac85a80924b1f870
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06890932B2

Reaction notes

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