Water → HCID 21075088, compound

HRID 1455360Notes

Reaction equation

HRID 1455360 reaction equation
[F:1][C:2]([F:25])([F:24])[S:3]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([O:21]CC)=[O:20])[CH:14]=2)[CH:10]=[CH:11][CH:12]=1)(=[O:5])=[O:4].[OH-].[Na+].O>C1COCC1>[F:24][C:2]([F:1])([F:25])[S:3]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([OH:21])=[O:20])[CH:14]=2)[CH:10]=[CH:11][CH:12]=1)(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 86596855HCID 86596855, compound

Product 1

HCID 21075088HCID 21075088, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Preparation H3, Step 3: 3′-Trifluoromethylsulfonamido-[1,1′-biphenyl]-3-carboxylic acid, ethyl ester (150 mg, 0.40 mmol, 1 eq.) and 1.000 N NaOH (0.80 mL, 0.80 mmol, 2 eq.) were dissolved in THF (5 mL) at room temperature and stirred for 20 hours. Little reaction. Added 100 mg of NaOH and heated at 50° C. for 20 hours. Worked up by adding water then rinsing 2 times with diethyl ether. The aqueous layer's pH was adjusted to 3 with 1N HCl. The acidic aqueous layer was extracted 3 times with ethyl acetate. The ethyl acetate layers were combined, dried over sodium sulfate and stripped to give 3′-trifluoromethylsulfonamido-[1,1′-biphenyl]-3-carboxylic acid (90 mg) of an amber solid. Yield=65%. Mass Spec (ESI) detects (M+H)+=344.0.

Workup

  1. customPreparation H3, Step 3
  2. customLittle reaction
  3. washthen rinsing 2 times with diethyl ether
  4. extractionThe acidic aqueous layer was extracted 3 times with ethyl acetate
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-78b9f346bc074d11892bffd832329456
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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