Ethyl Acetate → HCID 19102788, compound

HRID 1198695Notes

Reaction equation

HRID 1198695 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[S:30](=[O:37])(=[O:36])[NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:20][C:19]=2[F:38])[C:13]([CH2:39][CH2:40][CH2:41][CH3:42])=[N:12]1.[OH-].[Na+].C(OCC)(=O)C>C1COCC1.Cl>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([N:11]2[C:15](=[O:16])[N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[S:30](=[O:37])(=[O:36])[NH:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[CH:20][C:19]=3[F:38])[C:13]([CH2:39][CH2:40][CH2:41][CH3:42])=[N:12]2)[CH:4]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 103494052-(2-Bromo-5-nitrophenyl)-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 19102788HCID 19102788, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 200 mg (0.303 mmol) of 2-(2-bromo-5-nitrophenyl)-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step C) in 3.5 mL of THF was cooled to 0° C. and treated dropwise with a solution of 542 mg (2.4 mmol) of stannous chloride dihydrate in 1.5 mL of concentrated hydrochloric acid. After 45 minutes, the mixture was added to a vigorously stirred mixture of 50% NaOH and ice. Ethyl acetate (15 mL) was added, and the mixture was stirred at 0° C. for 1.5 hours. The phases were separated, and the aqueous fraction was re-extracted twice with ethyl acetate. The combined organic fractions were washed with water and brine and dried over anhydrous Na2SO4. The filtered solution was concentrated, and the residue was flash chromatographed on silica gel to give 131 mg (68%) of the title compound as a stiff, off-white foam, mp 103°-105° C.; homogeneous by TLC (95:5 CH2Cl2 --MeOH); mass spectrum (FAB) m/e 629, 631 (M+1)+.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous fraction was re-extracted twice with ethyl acetate
  3. washThe combined organic fractions were washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe filtered solution was concentrated
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-edb8436370164420b48b4f6103cc0c8f
Source dataset
uspto-grants-1994_01
Patent number
US05281614

Reaction notes

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