Acetic Acid → HCID 16732764, compound

HRID 1992806Notes

Reaction equation

HRID 1992806 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:20]=[CH:19][C:8](/[CH:9]=[N:10]/[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:7][CH:6]=1)=[O:4].CO.CC(O)=O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])=[CH:19][CH:20]=1)=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 6910008HCID 6910008, compound

Product 1

HCID 16732764HCID 16732764, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the intermediate from step B (8.4 g, 30.18 mmol) in THF (150 mL) was added methanol (15 mL), Na(CN)BH3 (5.7 g, 90.54 mmol) and AcOH (30 mL). The resulting solution was stirred at room temperature for 48 hours. The reaction was concentrated in vacuo. To the residue was added 1 M Na2CO3 solution (800 mL) and extracted with ether (3×). The organic layer was dried over anhydrous Na2SO4 filtered and concentrated in vacuo to give the desired product as a white solid. 1H NMR (CDCl3, 500 MHz): 8.04 (d, J=8.2 Hz, 2H), 7.46 (d, J=8.2 Hz, 2H), 4.08 (s, 2H), 3.94 (s, 3H), 1.49 (s,9H). LC-MS=2.43; (M+H−56)=224.9.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionTo the residue was added 1 M Na2CO3 solution (800 mL)
  3. extractionextracted with ether (3×)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be81e848de564f7ca447c78d1aad294e
Source dataset
uspto-grants-2010_01
Patent number
US07649009B2

Reaction notes

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