Trifluoroacetic acid → HCID 86681761, compound

HRID 571342Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N+:4]([O-:41])[CH:5]=[C:6]([Cl:40])[C:7]=1[CH2:8][C@@H:9]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH:32]([F:34])[F:33])=[C:27]([O:35]CC2CC2)[CH:26]=1)[O:10][C:11](=[O:24])[CH2:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23].FC(F)(F)C(O)=O>>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:41])[CH:5]=[C:6]([Cl:40])[C:7]=1[CH2:8][C@@H:9]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH:32]([F:34])[F:33])=[C:27]([OH:35])[CH:26]=1)[O:10][C:11](=[O:24])[CH2:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 71553904HCID 71553904, compound

Product 1

HCID 86681761HCID 86681761, compoundYield 66.3%

Procedure

A solution of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(1,3-dioxoisoindolin-2-yl)acetoxy)ethyl)pyridine 1-oxide (500 mg, 0.823 mmol) (prepared in analogous manner as described in Example 4, Scheme 4) in 2,2,2-trifluoroacetic acid (7.5 ml, 0.823 mmol) was stirred at RT for 8 hours. Then the solvent was evaporated under vacuum, and the residue was taken up several times with AcOEt/Et20 and evaporated under reduced pressure to afford 302 mg of the title compound (66% yield).

Workup

customThen the solvent was evaporated under vacuum
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-38a1a2b3275f4729ba1990240a45d6d1
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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