Sodium ethoxide → HCID 57905239, compound

HRID 1093110Notes

Reaction equation

HRID 1093110 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[N:14]([C:15](=[O:26])[C:16]=1[O:17]C(=O)C1C=CC=CC=1)[CH2:13][CH:12]1[CH2:27][CH2:28][C:9]2([O:29][CH2:30][CH2:31][O:32]C(=O)C2C=CC=CC=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2].C([O-])C.[Na+]>C1COCC1.CCO.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[N:14]([C:15](=[O:26])[C:16]=1[OH:17])[CH2:13][CH:12]1[CH2:27][CH2:28][C:9]2([O:29][CH2:30][CH2:31][OH:32])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 2723922Sodium ethoxideHCID 57904732HCID 57904732, compound

Product 1

HCID 57905239HCID 57905239, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent3×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

At room temperature, to a cold (ice-cooling) and stirred solution of 5-benzoyloxy-1-(2-benzoyloxy-ethoxy)-6-oxo-3,7-diazatricyclo[7.2.2.02,7]trideca-2,4-diene-4-carboxylic acid ethyl ester (330 mg, 0.604 mmol) in THF (6 mL) and EtOH (3.00 mL) was added 21% sodium ethanolate in EtOH (0.676 mL, 1.81 mmol) diluted with EtOH (3 mL) and the mixture stirred under N2 for 1 h. The mixture was diluted with ethyl acetate (10 mL) and extracted with water (10 mL×2). The aqueous extracts were acidified with 1N-HCl (3 mL) and extracted with ethyl acetate (10 mL×5). The ethyl acetate extracts were washed with brine, dried (Na2SO4) and concentrated to provide the title compound (130 mg, 0.38 mmol; 64% yield) as an oil: HPLC: retention time=1.33 min (area percent=95%); LCMS: m/z 339 (M+H); 1H NMR (500 MHz, CDCl3) δ ppm 1.43 (3H, t, J=7.2 Hz), 1.65 (2H, dt, J=12.3, 6.2 Hz), 1.85-1.97 (2H, m), 1.99-2.17 (4H, m), 2.46 (1H, brs), 3.60 (2H, t, J=4 Hz), 3.75 (2H, d, J=4.1 Hz), 4.06-4.15 (2H, m), 4.45 (2H, q, J=7.0 Hz), 10.48 (1H, brs); 13C NMR (126 MHz, CDCl3) δ ppm 14.0, 23.2, 27.6, 30.5, 53.9, 62.0, 63.2, 65.3, 76.7, 124.1, 148.2, 154.3, 159.7, 169.1.

Workup

  1. extractionextracted with water (10 mL×2)
  2. extractionextracted with ethyl acetate (10 mL×5)
  3. washThe ethyl acetate extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6ef645e56ace452f88ff840847617aaa
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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