Trifluoroacetic acid methylene chloride → HCID 46899330, compound

HRID 68592Notes

Reaction equation

HRID 68592 reaction equation
C(O)(C(F)(F)F)=O.C(Cl)Cl.[C:11]([C:13]1[CH:14]=[C:15]([C:19]2[CH:33]=[C:32]([CH2:34][NH:35][S:36]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[CH:31]=[CH:30][C:20]=2[O:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])[CH:16]=[CH:17][CH:18]=1)#[N:12]>>[C:11]([C:13]1[CH:14]=[C:15]([C:19]2[CH:33]=[C:32]([CH2:34][NH:35][S:36]([C:39]3[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=3)(=[O:38])=[O:37])[CH:31]=[CH:30][C:20]=2[O:21][CH2:22][C:23]([OH:25])=[O:24])[CH:16]=[CH:17][CH:18]=1)#[N:12]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 66868549HCID 66868549, compound

Product 1

HCID 46899330HCID 46899330, compoundYield 82%

Procedure

To a solution of TFA/DCM (1:3, 6 mL) was added t-butyl 2-(2-(3-cyanophenyl)-4-((4-fluorophenylsulfonamido)methyl)phenoxy)acetate (8) (51 mg, 0.10 mmol, 1 eq) and the mixture was stirred at room temperature for 2 h. The organic solvent was removed in vacuo and the crude product was purified by reversed phase preparative HPLC to give 36 mg (82%) of 2-(2-(3-cyanophenyl)-4-((4-fluorophenylsulfonamido)methyl)phenoxy)acetic acid (Example 9).

Workup

  1. customThe organic solvent was removed in vacuo
  2. customthe crude product was purified by reversed phase preparative HPLC

Sources & evidence

ORD record
ord-89ce0b42cbdb409f82ad562047c4debf
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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