Acetic Acid → HCID 46939473, compound

HRID 2181576Notes

Reaction equation

HRID 2181576 reaction equation
[ClH:1].O[NH:3][C:4]([C:6]1([S:15]([C:18]2[CH:23]=[CH:22][C:21](SC3C=CC=CC=3)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:11][CH2:10][N:9](CC#C)[CH2:8][CH2:7]1)=[O:5].[F:31][C:32]([F:37])([F:36])[C:33](O)=O.C(N([CH2:43][CH3:44])CC)C.[CH3:45][C:46]([CH3:48])=O.[C:49]([BH3-])#N.[Na+].[C:53]([OH:56])(=O)[CH3:54].[OH-:57].[Na+]>C(Cl)Cl>[ClH:1].[OH:57][NH:3][C:4]([C:6]1([S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:56][C:53]3[CH:54]=[CH:49][C:33]([C:32]([F:37])([F:36])[F:31])=[CH:44][CH:43]=3)=[CH:20][CH:19]=2)(=[O:16])=[O:17])[CH2:11][CH2:10][N:9]([CH:46]([CH3:48])[CH3:45])[CH2:8][CH2:7]1)=[O:5]

Participants

9

Reactant 7

HCID 176Acetic AcidHCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 9890734HCID 9890734, compound

Product 1

HCID 46939473HCID 46939473, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Part A: To a solution of the product of Example 9, Part D (30.0 g, 80.8 mmol) in methylene chloride (100 mL) was added trifluoroacetic acid (30 mL) in methylene chloride (40 mL). The solution was stirred at ambient temperature for two hours. The solution was concentrated in vacuo. To the residue dissolved in methylene chloride (150 mL) at zero degrees Celsius were added triethylamine (28.0 mL, 277 mmol), acetone (24.0 mL, 413 mmol), sodium cyanoborohydride (68 g, 323.1 mmol) and acetic acid (18.5 mL, 308 mmol). The reaction mixture was stirred at ambient temperature for 18 hours. The solution was diluted with 1N NaOH and extracted with ethyl ether. The organic layer was washed with 1N NaOH, water, saturated NaCl and dried over MgSO4, filtered and concentrated in vacuo to provided the desired isopropylamine (21.03 g, 72%).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionTo the residue dissolved in methylene chloride (150 mL) at zero degrees Celsius
  3. stirringThe reaction mixture was stirred at ambient temperature for 18 hours
  4. extractionextracted with ethyl ether
  5. washThe organic layer was washed with 1N NaOH, water, saturated NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1047ba75c00949c5803578afbc3781f2
Source dataset
uspto-grants-2005_05
Patent number
US06890937B2

Reaction notes

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