Trifluoroacetic acid → HCID 19348621, compound

HRID 1418209Notes

Reaction equation

FC(F)(F)C(O)=O.[C:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][C:13]=1[NH:22][C:23](=[O:48])[CH2:24][CH:25]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]([O:41]C(C)(C)C)=[O:40])=[CH:33][C:32]=1[O:46][CH3:47])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([CH3:11])([CH3:10])[CH3:9].C1(OC)C=CC=CC=1>C(Cl)Cl>[C:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][C:13]=1[NH:22][C:23](=[O:48])[CH2:24][CH:25]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]([OH:41])=[O:40])=[CH:33][C:32]=1[O:46][CH3:47])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([CH3:9])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 30 °C

Procedure

1.0 ml (15.0 mmol) of trifluoroacetic acid was added to a solution of 575 mg (1.01 mmol) of N-(2-t-butyl-5-methoxycarbonylphenyl)-3-(4-t-butoxycarbonylmethoxy-2-methoxyphenyl)octanamide [prepared as described in step (i) above] and 241 μl (2.22 mmol) of anisole in 15 ml of methylene chloride, and the resulting mixture was stirred overnight at 30° C. At the end of this time, the reaction mixture was freed from the solvent and excess reagents by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 50 g of silica gel using ethyl acetate as the eluent, to give 506 mg (yield 98%) of the title carboxylic acid derivative as a foam-like substance.

Workup

distillationAt the end of this time, the reaction mixture was freed from the solvent and excess reagents by distillation under reduced pressure
customthe resulting residue was purified by column chromatography through 50 g of silica gel

Sources & evidence

ORD record: ord-d2dfc3045dfb468e931115cc38d2372a
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05880147

Reaction notes

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