Trifluoroacetic acid → [(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]3-formyl-2-hydroxy-benzoate

HRID 1497995Notes

Reaction equation

C(O)(C(F)(F)F)=O.[CH:8]1([CH2:11][O:12][C:13]2[CH:14]=[C:15]([C@@H:23]([O:34][C:35](=[O:52])[C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([CH:42]=[O:43])[C:37]=3[O:44]CC3C=CC=CC=3)[CH2:24][C:25]3[C:30]([Cl:31])=[CH:29][N+:28]([O-:32])=[CH:27][C:26]=3[Cl:33])[CH:16]=[CH:17][C:18]=2[O:19][CH:20]([F:22])[F:21])[CH2:10][CH2:9]1>C1(C)C=CC=CC=1.C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH:8]1([CH2:11][O:12][C:13]2[CH:14]=[C:15]([C@@H:23]([O:34][C:35](=[O:52])[C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([CH:42]=[O:43])[C:37]=3[OH:44])[CH2:24][C:25]3[C:30]([Cl:31])=[CH:29][N+:28]([O-:32])=[CH:27][C:26]=3[Cl:33])[CH:16]=[CH:17][C:18]=2[O:19][CH:20]([F:21])[F:22])[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 0 °C

Procedure

TFA (0.4 mL) was carefully added to a solution of [(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]2-benzyloxy-3-formyl-benzoate (116 mg, 0.18 mmol) in toluene (0.8 mL) at 0° C. The resulting mixture was stirred at 0° C. for 50 minutes. The solution was diluted with DCM (20 mL) and sat. NaHCO3 (20 mL). The layers were separated over a hydrophobit frit and the organic phase concentrated in vacuo, the residue azeotroped with toluene to dryness. The yellow gum (120 mg) was used in the next step without further purification.

Workup

customThe layers were separated over a hydrophobit frit
concentrationthe organic phase concentrated in vacuo
customthe residue azeotroped with toluene to dryness
customThe yellow gum (120 mg) was used in the next step without further purification

Sources & evidence

ORD record: ord-8d106443b25446c3a51954e4cf83e1b1
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199980B2

Reaction notes

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