Acetic Acid → HCID 10361107, compound

HRID 1768617Notes

Reaction equation

HRID 1768617 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[S:12]([NH:15][C:16]1[O:20][N:19]=[C:18]([CH3:21])[C:17]=1[CH3:22])(=[O:14])=[O:13].[CH3:23][C:24]([CH3:26])=O.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH3:23][CH:24]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[S:12]([NH:15][C:16]1[O:20][N:19]=[C:18]([CH3:21])[C:17]=1[CH3:22])(=[O:14])=[O:13])[CH3:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 10087191HCID 10087191, compound

Product 1

HCID 10361107HCID 10361107, compoundYield 123.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example 3 (0.150 g, 0.473 mmol) in 10 mL of methanol, was added acetone (0.035 g, 0.473 mmol). The resulting clear yellow solution was stirred for 45 minutes. Sodium cyanoborohydride (0.058 g, 0.95 mmol) and acetic acid (0.172 g, 2.85 mmol) were added and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, taken up in 20 mL of water and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine (1×35 mL), dried (magnesium sulfate) and concentrated in vacuo to give 0.21 g of a yellow solid. This material was chromatographed (50 g Merck silica gel) using ethyl acetate:hexanes (1:1) as the eluant to give 0.101 g (60%) of Example 18 as a yellow solid.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. washThe combined organic layers were washed with brine (1×35 mL)
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d98e6324dad44269b7f9b03145b3d039
Source dataset
uspto-grants-1995_01
Patent number
US05378715

Reaction notes

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