Water → HCID 136335114, compound

HRID 2375234Notes

Reaction equation

HRID 2375234 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:6]=1)(=O)C.O>CO>[CH2:14]([O:13][N:12]=[C:11]([C:8]1[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=1)[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 962WaterHCID 76837484HCID 76837484, compound

Product 1

HCID 136335114HCID 136335114, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 4-{(benzyloxy)[(benzyloxy)imino]methyl}phenyl acetate (19) (1.671 g, 4.45 mmol) in dry methanol (30 ml) 3.43 N sodium methoxide solution in methanol (1.3 ml, 4.46 mmol) was added and the reaction mixture was stirred at ambient temperature until the starting material disappeared (ca. 1 hour). The mixture was poured into a mixture of water (60 ml) and saturated NaH2PO4 (30 ml), and extracted with ethyl acetate (2×25 ml). The extract was washed with brine (30 ml) and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silicagel (50 g) with benzene-ethyl acetate (9:1) as eluent to give benzyl N-(benzyloxy)-4-hydroxybenzenecarboximidoate (15) (1.428 g, 96%) as an interchangeable mixture (2D TLC) of 2 isomers with Rf 0.62 and Rf 0.49 (toluene-ethyl acetate, 9:1). Major (less polar) isomer of 15: 1H NMR (DMSO-d6, HMDSO) δ: 4.99 (2H, s); 5.09 (2H, s); 6.80 (2H, d, J=8.7 Hz); 7.27-7.53 (10H, m); 7.67 (2H, d, J=8.7 Hz); 9.96 (1H, s). Minor (more polar) isomer of 15: 1H NMR (DMSO-d6, HMDSO) δ: 5.06 (2H, s); 5.24 (2H, s); 6.75 (2H, d, J=8.6 Hz); 7.27-7.53 (10H, m); 7.67 (2H, d, J=8.6 Hz); 9.84 (1H, s).

Workup

  1. custom(ca. 1 hour)
  2. extractionextracted with ethyl acetate (2×25 ml)
  3. washThe extract was washed with brine (30 ml)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe residue was chromatographed on silicagel (50 g) with benzene-ethyl acetate (9:1) as eluent

Sources & evidence

ORD record
ord-2c8cc492ec9f4f82809f748a10b27092
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

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