Acetic Acid → HCID 6910008, compound

HRID 1992805Notes

Reaction equation

HRID 1992805 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])[NH:14][NH2:15].CC(O)=O>ClC(Cl)C>[CH3:4][O:3][C:1]([C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[N:15]/[NH:14][C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 15294Methyl 4-FormylbenzoateHCID 70091tert-Butyl carbazate

Product 1

HCID 6910008HCID 6910008, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 4-carbomethoxy benzaldehyde (5.0 g, 36.46 mmol) in dichloroethane (40 mL) was added tert-butyl carbazate (4.03 g, 30.46 mmol) followed by AcOH (1.74 mL, 30.46 mmol). After 1.5 hours, the reaction was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with saturated NaHCO3, solution, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. This material was used without any further purification in the next step. 1H NMR (CDCl3, 500 MHz): 8.03 (d, J=8.5 Hz, 3H), 7.93 (bs, 1H), 7.8 (d, J=8.2 Hz, 2H), 3.96 (s, 3H), 1.58 (s, 9H). LC-MS=3.1; (M+H−56)=223.1.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated NaHCO3, solution
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThis material was used without any further purification in the next step

Sources & evidence

ORD record
ord-4a2b4bb77902417ca17d3f2f361ab7bb
Source dataset
uspto-grants-2010_01
Patent number
US07649009B2

Reaction notes

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