Acetaldehyde → HCID 22103791, compound

HRID 1457199Notes

Reaction equation

HRID 1457199 reaction equation
C([BH3-])#N.[Na+].Cl.[CH3:6][C:7]1[C:11]([CH3:12])=[C:10]([NH:13][S:14]([C:17]2[C:18]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[O:30][CH:31]=[CH:32][N:33]=4)=[CH:25][C:24]=3[CH2:34][NH:35][CH2:36][C:37]([F:40])([F:39])[F:38])=[CH:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[O:9][N:8]=1.[CH:41](=O)[CH3:42]>CO>[CH3:6][C:7]1[C:11]([CH3:12])=[C:10]([NH:13][S:14]([C:17]2[C:18]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[O:30][CH:31]=[CH:32][N:33]=4)=[CH:25][C:24]=3[CH2:34][N:35]([CH2:41][CH3:42])[CH2:36][C:37]([F:40])([F:39])[F:38])=[CH:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[O:9][N:8]=1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 69848285HCID 69848285, compound

Product 1

HCID 22103791HCID 22103791, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (13 mg; 0.20 mmol) was added to a mixture of N-(3,4-dimethyl-5-isoxazolyl)-4'-(2-oxazolyl)-2'-[[(2,2,2-trifluoroethyl)amino]methyl][1,1'-biphenyl]-2-sulfonamide, monohydrochloride (55 mg; 0.10 mmol, prepared as in Example 45), 100 mg of 3 Å molecular sieves and acetaldehyde (0.10 ml; 1.80 mmol) in 1 ml of methanol at room temperature. After stirring for 18 hours at room temperature, the reaction mixture was filtered through a nylon syringe filter. The filtrate was concentrated and the residue was partitioned between EtOAc (20 ml) and saturated NaHCO3 solution (20 ml), the aqueous layer was extracted with EtOAc (20 ml). The combined organic layers were washed with brine (25 ml), dried (MgSO4) and concentrated. The residue was chromatographed on a 2.5×6 cm silica gel column, using EtOAc:Hex, 1:1 as the mobile phase. The pure fractions were concentrated to an oil that was dissolved in ~0.2 ml of MeOH. Water (3 ml) was added and the turbid mixture was frozen. Lyophilization afforded 24 mg (49%) of the title compound of this Example as a white solid.

Workup

  1. filtrationthe reaction mixture was filtered through a nylon syringe
  2. filtrationfilter
  3. concentrationThe filtrate was concentrated
  4. customthe residue was partitioned between EtOAc (20 ml) and saturated NaHCO3 solution (20 ml)
  5. extractionthe aqueous layer was extracted with EtOAc (20 ml)
  6. washThe combined organic layers were washed with brine (25 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was chromatographed on a 2.5×6 cm silica gel column
  10. concentrationThe pure fractions were concentrated to an oil that
  11. dissolutionwas dissolved in ~0.2 ml of MeOH
  12. additionWater (3 ml) was added
  13. temperaturethe turbid mixture was frozen

Sources & evidence

ORD record
ord-4902e003effd40be91cce6aacfa2d8c9
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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