Potassium sodium tartarate → HCID 58268201, compound

HRID 1898255Notes

Reaction equation

HRID 1898255 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[CH:23]=[CH:22][C:15]([C:16](N(OC)C)=[O:17])=[C:14]([N:24]([S:28]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([C:38]([F:41])([F:40])[F:39])[CH:32]=2)(=[O:30])=[O:29])[CH2:25][O:26][CH3:27])[CH:13]=1.C([O-])(=O)C(C(C([O-])=O)O)O.[K+].[Na+]>C1COCC1>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([S:28]([N:24]([C:14]2[CH:13]=[C:12]([Cl:11])[CH:23]=[CH:22][C:15]=2[CH:16]=[O:17])[CH2:25][O:26][CH3:27])(=[O:29])=[O:30])=[CH:32][C:33]=1[C:38]([F:40])([F:41])[F:39]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 58268093HCID 58268093, compound

Product 1

HCID 58268201HCID 58268201, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutylaluminium hydride (DIBAL-H, 1.5 M solution in toluene, 0.73 mL, 1.1 mmol) was added drop wise to a solution of 4-chloro-2-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-N-methoxy-N-methyl-benzamide (220 mg, 0.44 mmol) in THF (3 mL) at −78° C. and stirred at the same temperature for an hour. Saturated aqueous sodium potassium tartarate solution (10 mL) was added slowly, warmed to room temperature, extracted with EtOAc (2×25 mL), dried (anhydrous Na2SO4) and concentrated. Obtained residue was purified by column chromatography (SiO2, 50% EtOAc-hexanes) to obtain 4-chloro-N-(5-chloro-2-formyl-phenyl)-N-methoxymethyl-3-trifluoromethyl-benzene sulfonamide (120 mg) in 62% yield. ESMS m/z (relative intensity): 410 (M−31)+ (95), 464 (M+Na)+ (100).

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. dry with materialdried (anhydrous Na2SO4)
  3. concentrationconcentrated
  4. customObtained residue was purified by column chromatography (SiO2, 50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-43be614e21924460a427953f6ab5a7b3
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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