tert-butyl 2-(3-fluoro-5-methoxyphenyl)-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxyacetate → 2-(3-fluoro-5-methoxyphenyl)-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxyacetic acid

HRID 68595Notes

Reaction equation

HRID 68595 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:24]=[C:23]([CH2:25][N:26]([CH3:38])[S:27]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([Cl:37])[CH:31]=3)(=[O:29])=[O:28])[CH:22]=[CH:21][C:11]=2[O:12][CH2:13][C:14]([O:16]C(C)(C)C)=[O:15])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:24]=[C:23]([CH2:25][N:26]([CH3:38])[S:27]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([Cl:37])[CH:31]=3)(=[O:29])=[O:28])[CH:22]=[CH:21][C:11]=2[O:12][CH2:13][C:14]([OH:16])=[O:15])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

3

Reactant 1

HCID 67528984tert-butyl 2-(3-fluoro-5-methoxyphenyl)-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxyacetate

Product 1

HCID 675278512-(3-fluoro-5-methoxyphenyl)-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxyacetic acidYield 67%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

To a solution of TFA/DCM (1:3, 80 mL) was added tert-butyl 2-(3-fluoro-5-methoxyphenyl)-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxyacetate (11) (15 g, 26 mol) and the mixture was stirred at room temperature for 2 h. The solvent was evaporated and the resulting solid was rinsed by petroleum ether/EtOAc (10:1 mixture) to yield 2-(3-fluoro-5-methoxyphenyl)-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxyacetic acid (Example 37) (9 g, 67%). 1HNMR (CD3CN, 300 MHz): δ 7.93 (d, 1H), 7.78 (m, 1H), 7.45 (t, 1H), 7.20 (m, 2H), 6.95 (m, 3H), 6.67 (d, 1H), 4.65 (s, 2H), 4.15 (s, 2H), 3.81 (s, 3H), 2.61 (s, 3H). MS (ES-API): MH−=510.0. HPLC (Method A) tR=2.28 min.

Workup

  1. customThe solvent was evaporated
  2. washthe resulting solid was rinsed by petroleum ether/EtOAc (10:1 mixture)

Sources & evidence

ORD record
ord-808284d241f54ecf828394e1db5ca876
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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