Acetic Acid → HCID 11071062, compound

HRID 1457197Notes

Reaction equation

HRID 1457197 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[CH:20][C:19]=3[CH:29]=O)=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])[O:4][N:3]=1.[CH2:31]([NH:35][CH3:36])[CH:32]([CH3:34])[CH3:33].CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[CH:20][C:19]=3[CH2:29][N:35]([CH3:36])[CH2:31][CH:32]([CH3:34])[CH3:33])=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:10])=[O:11])[O:4][N:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 12249N-MethylisobutylamineHCID 5049666Sodium triacetoxyborohydrideHCID 10740948HCID 10740948, compound

Product 1

HCID 11071062HCID 11071062, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After briskly stirring a mixture of N-(3,4-dimethyl-5-isoxazolyl)-2'-formyl-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide (100 mg; 0.24 mmol; prepared as in Step (F) of Example 21), isobutylmethylamine (0.087 ml; 0.71 mmol), AcOH (0.08 ml; 1.34 mmol) and 3 Å molecular sieves (670 mg) in 2 ml of CH2Cl2 for 1 hour at room temperature, sodium triacetoxyborohydride (150 mg; 0.71 mmol) was added. After stirring 18 hours at room temperature, the reaction mixture was filtered through celite and the filtrate was partitioned between EtOAc (40 ml) and saturated NaHCO3 solution (20 ml). The organic layer was washed with water (20 ml) followed by brine (20 ml). Drying (Na2 SO4) and concentration afforded a residue that was chromatographed on a 2.5×12 cm silica gel column using a stepwise gradient of 300 ml @CH2Cl2 to 5% MeOH/CH2Cl2 in 1% increments. The pure fractions were concentrated to afford 88 mg of the title compound of this Example as a white powder.

Workup

  1. stirringAfter stirring 18 hours at room temperature
  2. filtrationthe reaction mixture was filtered through celite
  3. customthe filtrate was partitioned between EtOAc (40 ml) and saturated NaHCO3 solution (20 ml)
  4. washThe organic layer was washed with water (20 ml)
  5. customDrying
  6. concentration(Na2 SO4) and concentration
  7. customafforded a residue that
  8. customwas chromatographed on a 2.5×12 cm silica gel column
  9. concentrationThe pure fractions were concentrated

Sources & evidence

ORD record
ord-ecce0dde296a4731b6899e17d71edfc4
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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