Water → HCID 10596534, compound

HRID 374883Notes

Reaction equation

HRID 374883 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([S:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:6]=[CH:5][C:4]=1[NH:18][C:19](=[O:27])[C:20]([OH:26])([CH3:25])[C:21]([F:24])([F:23])[F:22].B(Br)(Br)Br.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[C:7]([S:9]([C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)(=[O:10])=[O:11])[CH:6]=[CH:5][C:4]=1[NH:18][C:19](=[O:27])[C:20]([OH:26])([CH3:25])[C:21]([F:23])([F:24])[F:22]

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 10573268HCID 10573268, compound

Product 1

HCID 10596534HCID 10596534, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of N-[2-methoxy-4-(4-pyridylsulfonyl)phenyl]-3,3,3,-trifluoro-2-hydroxy-2-methyl propanamide (1.30 g) and sieve dried methylene chloride (50 mL) was added boron tribromide (1.6 mL of a 1.0M solution in methylene chloride), and the mixture (a gummy ball of material and solvent) was stirred at reflux for 2 hours and then stirred overnight at room temperature. The reaction mixture was poured into water, made basic with saturated sodium bicarbonate solution and extracted with methylene chloride (2×250 mL; discarded) followed by ethyl acetate (100 mL). The ethyl acetate solution was dried, filtered, evaporated to a brown oil and purified by chromatography twice (eluent ethyl acetate and eluent methylene chloride-ethyl acetate (1:4)) to yield the title compound (0.15 g); mp 218°-220° C. Analysis for C15H13F3N2O5S: Calculated: C, 46.16; H, 3.36; N, 7.18: Found: C, 45.87; H, 3.47; N, 6.91. ##STR2##

Workup

  1. temperatureat reflux for 2 hours
  2. stirringstirred overnight at room temperature
  3. extractionextracted with methylene chloride (2×250 mL; discarded)
  4. dry with materialThe ethyl acetate solution was dried
  5. filtrationfiltered
  6. customevaporated to a brown oil
  7. custompurified by chromatography twice (eluent ethyl acetate and eluent methylene chloride-ethyl acetate (1:4))

Sources & evidence

ORD record
ord-926e120ad5f24d7cbd0046e2b562d818
Source dataset
uspto-grants-1996_01
Patent number
US05482969

Reaction notes

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