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 1529540Notes

Reaction equation

C(O)(C(F)(F)F)=O.C([O:15][C:16]1[C:50]([CH:51]=[O:52])=[CH:49][CH:48]=[CH:47][C:17]=1[C:18]([O:20][C@H:21]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH:39]([F:41])[F:40])=[C:34]([O:42][CH2:43][CH:44]2[CH2:46][CH2:45]2)[CH:33]=1)[CH2:22][C:23]1[C:28]([Cl:29])=[CH:27][N+:26]([O-:30])=[CH:25][C:24]=1[Cl:31])=[O:19])C1C=CC=CC=1>C1(C)C=CC=CC=1.C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH:51]([C:50]1[C:16]([OH:15])=[C:17]([CH:47]=[CH:48][CH:49]=1)[C:18]([O:20][C@H:21]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH:39]([F:40])[F:41])=[C:34]([O:42][CH2:43][CH:44]2[CH2:46][CH2:45]2)[CH:33]=1)[CH2:22][C:23]1[C:24]([Cl:31])=[CH:25][N+:26]([O-:30])=[CH:27][C:28]=1[Cl:29])=[O:19])=[O:52]

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 fit 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 fit
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-5b7fca5398344aeb836893a048e26b0e
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090606B2

Reaction notes

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