Acetic Acid → HCID 67186685, compound

HRID 735854Notes

Reaction equation

HRID 735854 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:7])=[CH:4][CH:3]=1.C(O)(=O)C.[CH:27]([C:29]1[CH:38]=[CH:37][CH:36]=[CH:35][C:30]=1[C:31]([O:33][CH3:34])=[O:32])=O.[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>C(O)C>[CH2:9]([NH:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:27][C:29]2[CH:38]=[CH:37][CH:36]=[CH:35][C:30]=2[C:31]([O:33][CH3:34])=[O:32])=[CH:22][CH:21]=1)=[O:7])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 243003Methyl 2-formylbenzoateHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 22767596HCID 22767596, compound

Product 1

HCID 67186685HCID 67186685, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-amino-N-dodecylbenzamide (0.304 g, 1.0 mmol), acetic acid (0.060 g, 1.0 mmol) and methyl 2-formylbenzoate (0.164 g, 1.0 mmol) in ethanol (2 mL) was added at once NaBH3CN (0.075 g, 1.20 mmol). The resulting mixture was stirred overnight at rt. A saturated solution of NaHCO3 (10 mL) was added to the reaction mixture, the aqueous layer was separated and extracted with DCM. The combined organic layers were dried over MgSO4, filtered and concentrated to give a colorless oil. This crude product was purified by column chromatography over silica gel to give the title compound as a colorless oil (0.212 g, 47%). M+(LC/MS(ESI)): 453.6. HPLC (Condition A), Rt: 6.64 min (HPLC purity: 100%).

Workup

  1. customthe aqueous layer was separated
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a colorless oil
  7. customThis crude product was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-e58720b2e7074588b3a64999c7d2df3c
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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