HCID 66868666, compound → HCID 46898868, compound

HRID 68588Notes

Reaction equation

HRID 68588 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:23]=[C:22]([CH2:24][N:25]([CH3:36])[S:26]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH:21]=[CH:20][C:10]=2[O:11][CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[CH:6]=[CH:7][CH:8]=1)#[N:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:23]=[C:22]([CH2:24][N:25]([CH3:36])[S:26]([C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)(=[O:28])=[O:27])[CH:21]=[CH:20][C:10]=2[O:11][CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 1

HCID 66868666HCID 66868666, compound

Product 1

HCID 46898868HCID 46898868, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

t-butyl 2-(2-(3-cyanophenyl)-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate (4) (780 mg; 1.53 mmol) was stirred in a mixture of TFA (15 mL) and DCM (30 mL) for 1 h. After concentration in vacuo, the residue was purified via reversed phase semi-preparative HPLC to yield 303 mg (43.6%) of 2-(2-(3-cyanophenyl)-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetic acid (Example 5) as a white solid. 1HNMR (CDCl3, 300 MHz): δ 7.84 (m, 3H), 7.75 (m, 1H), 7.61 (m, 1H), 7.50 (t, 1H), 7.24 (m, 3H), 6.85 (d, 1H), 4.69 (s, 2H), 4.13 (s, 2H), 2.63 (s, 3H).

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe residue was purified via reversed phase semi-preparative HPLC

Sources & evidence

ORD record
ord-31b96ab7fd58449299a43fe9aa6fa686
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

Loading…