Lithium Hydroxide → HCID 46898402, compound

HRID 68601Notes

Reaction equation

HRID 68601 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C:9]2[CH:20]=[C:19]([CH:21]([N:23]([CH3:34])[S:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH3:22])[CH:18]=[CH:17][C:10]=2[O:11][CH2:12][C:13]([O:15]C)=[O:14])[CH:6]=[CH:7][CH:8]=1.[OH-].[Li+]>CO.O>[F:36][C:2]([F:1])([F:35])[C:3]1[CH:4]=[C:5]([C:9]2[CH:20]=[C:19]([CH:21]([N:23]([CH3:34])[S:24]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)(=[O:26])=[O:25])[CH3:22])[CH:18]=[CH:17][C:10]=2[O:11][CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 70804820methyl 2-(2-(3-trifluoromethylphenyl)-4-(1-(4-fluoro-N-methylphenylsulfonamido)ethyl)phenoxy)acetate

Product 1

HCID 46898402HCID 46898402, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of methyl 2-(2-(3-trifluoromethylphenyl)-4-(1-(4-fluoro-N-methylphenylsulfonamido)ethyl)phenoxy)acetate (19) in MeOH/H2O (4/1) was added lithium hydroxide (2 eq) and the mixture was stirred at room temperature for 2 h. After concentrating in vacuo, the residue was purified via semi-preparative HPLC to give 21.9 mg, (15.2% from Intermediate 18) of 2-(2-(3-trifluoromethylphenyl)-4-(1-(4-fluoro-N-methylphenylsulfonamido)ethyl)phenoxy)acetic acid (Example 22) as white solid. 1HNMR (CDCl3, 400 MHz): δ 7.61 (s, 1H), 7.53 (m, 3H), 7.31 (m, 1H), 7.25 (m, 1H), 7.22 (m, 1H), 7.03 (m, 2H), 6.72 (d, 1H), 5.01 (m, 1H), 4.14 (s, 2H), 2.38 (s, 3H), 1.06 (d, 3H). MS (ES-API): M=323.1 (main fragment). HPLC (Method B) tR=3.43 min.

Workup

  1. concentrationAfter concentrating in vacuo
  2. customthe residue was purified via semi-preparative HPLC

Sources & evidence

ORD record
ord-955d6bc71f9a403193b4c6f7528e76d9
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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