Sulfamic Acid → 3-Methoxy-2'-(trifluoromethyl)[1,1'-biphenyl]-4-carboxylic acid

HRID 2184457Notes

Reaction equation

HRID 2184457 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])[CH:6]=[CH:7][C:8]=1[CH:9]=[O:10].S(=O)(=O)([OH:23])N.Cl([O-])=O.[Na+].CCCCCC>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:18])([F:19])[F:20])[CH:6]=[CH:7][C:8]=1[C:9]([OH:23])=[O:10]

Participants

7

Reactant 4

HCID 5987Sulfamic Acid2×HCID 8058HexaneHCID 22472940HCID 22472940, compoundHCID 23668197Sodium Chlorite2×

Product 1

HCID 224729293-Methoxy-2'-(trifluoromethyl)[1,1'-biphenyl]-4-carboxylic acidYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 3-methoxy2′-trifluoromethyl-[1,1′-biphenyl]-4-carboxaldehyde of Step B (0.95 g, 3.41 mmol) and sulfamic acid (0.43 g, 4.43 mmol) were dissolved in a mixture of tetrahydrofuran and water (1:1, v/v, 30 mL). Sodium chlorite (0.31 g, 4.43 mmol) was added under stirring, and the solution turned yellow. After 30 minutes, additional sodium chlorite and sulfamic acid were added, and the solution stirred an additional hour. The solution was then concentrated, and the residue partitioned between ethyl acetate and water. The ethyl acetate layer was dried and concentrated to yield an oil, which solidified upon trituration with hexane to provide the title compound (0.84 g) as a yellow solid, which was used as such in the next step.

Workup

  1. stirringthe solution stirred an additional hour
  2. concentrationThe solution was then concentrated
  3. customthe residue partitioned between ethyl acetate and water
  4. dry with materialThe ethyl acetate layer was dried
  5. concentrationconcentrated
  6. customto yield an oil, which

Sources & evidence

ORD record
ord-7e09c62c371944e7b3552c2fe9db0ee0
Source dataset
uspto-grants-2005_05
Patent number
US06900200B2

Reaction notes

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