Lithium hydroxide, monohydrate → Ethyl-N-(2-carboxyphenoxy)acetimidate

HRID 971181Notes

Reaction equation

HRID 971181 reaction equation
O[Li].O.[CH2:4]([O:6][C:7](=[N:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([O:19]CC1C=CC=CC=1)=[O:18])[CH3:8])[CH3:5].C1COCC1.CO.O>O>[CH2:4]([O:6][C:7](=[N:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([OH:19])=[O:18])[CH3:8])[CH3:5]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21892291Methanol tetrahydrofuran waterHCID 72781090Ethyl-N-(2-benzyloxycarbonylphenoxy)acetimidate

Product 1

HCID 72810275Ethyl-N-(2-carboxyphenoxy)acetimidateYield 80.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

LiOH.H2O (431 mg, 10.3 mmol) was added to a solution of ethyl-N-(2-benzyloxycarbonylphenoxy)acetimidate 18 (802 mg, 2.56 mmol) in a 9/3/3 mL mixture of THF/MeOH/H2O and the reaction was stirred at room temperature. After 6 h the reaction was diluted with H2O (100 mL), washed with CH2Cl2 (4×30 mL), acidified to pH˜5.0-5.5 with 0.5 N HCl, and extracted with EtOAc (4×30 mL). The combined organics were washed with H2O (30 mL) and brine (30 mL), dried over Na2SO4, filtered, and concentrated to afford 20 as a white solid (459 mg, 80%). 1H-NMR (500 MHz, d6-Acetone) δ 1.34 (t, J=6.9 Hz, 3H), 2.18 (s, 3H), 4.20 (q, J=6.9 Hz, 2H), 7.02 (ddd, J=0.9, 7.3, 7.8 Hz, 1H), 7.51 (ddd, J=1.8, 7.3, 8.7 Hz, 1H), 7.60 (dd, J=0.9, 8.7 Hz, 1H) 7.86 (dd, J=1.8, 7.8 Hz, 1H); 13C-NMR (125 MHz, d6-Acetone) δ 14.6, 14.7, 63.8, 115.2, 118.5, 121.3, 132.4, 134.5, 160.2, 166.8, 167.4; ESI-MS 224 m/z [MH]+, C11H14NO4 requires 224.

Workup

  1. washwashed with CH2Cl2 (4×30 mL)
  2. extractionextracted with EtOAc (4×30 mL)
  3. washThe combined organics were washed with H2O (30 mL) and brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b131490c2af64b59a9e58636d422f960
Source dataset
uspto-grants-2007_12
Patent number
US07312361B2

Reaction notes

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