Sulfuric acid magnesium salt (1:1) → HCID 66712739, compound

HRID 1866349Notes

Reaction equation

HRID 1866349 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].S([O-])([O-])(=O)=O.[Mg+2].[CH2:15]([O:17][C:18](=[O:34])[C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][C:20]=1[CH:32]=O)[CH3:16]>ClCCl.C(N(CC)CC)C>[CH2:15]([O:17][C:18](=[O:34])[C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][C:20]=1[CH:32]=[N:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8])[CH3:16]

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 2723640Glycine ethyl ester, hydrochlorideHCID 86014539HCID 86014539, compound

Product 1

HCID 66712739HCID 66712739, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a dried flask with glycine ethyl ester hydrochloride salt (62 mg) was added anhydrous dichloromethane (2 mL), followed by triethylamine (124 μL). Then magnesium sulfate (pre-dried on high vacuum by heat gun, 100 mg) was added, followed by addition of a dichloromethane (1 mL) solution of 2-formyl-4-phenoxy-benzoic acid ethyl ester (120 mg). The flask of 2-formyl-4-phenoxy-benzoic acid ethyl ester was further rinsed with 0.5 mL of dichloromethane. The resulting mixture was stirred at room temperature under nitrogen for 15 h. The mixture was filtered and rinsed with dichloromethane. After removal of solvent, the reaction was diluted with ether (15 mL) and washed with brine twice and dried. Filtration and removal of solvent gave the title compound 160 mg as an oil with good purity. 1H NMR (200 MHz, CDCl3) δ 9.02 (d, J=1.2, 1H), 7.94 (d, J=8.6 Hz, 1H), 7.63 (d, J=2.4, 1H), 7.40-7.32 (m, 2H), 7.20-7.11 (m, 1H), 7.06-6.97 (m, 3H), 4.41 (s, 2H), 4.35 (q, J=7.0 Hz, 2H), 4.21 (q, J=7.4 Hz, 2H), 1.39 (t, J=7.0 Hz, 3H), 1.28 (t, J=7.0 Hz, 3H).

Workup

  1. washThe flask of 2-formyl-4-phenoxy-benzoic acid ethyl ester was further rinsed with 0.5 mL of dichloromethane
  2. filtrationThe mixture was filtered
  3. washrinsed with dichloromethane
  4. customAfter removal of solvent
  5. additionthe reaction was diluted with ether (15 mL)
  6. washwashed with brine twice
  7. customdried
  8. filtrationFiltration and removal of solvent

Sources & evidence

ORD record
ord-35851ada2d2f462ba688c38f49d4231f
Source dataset
uspto-grants-2009_12
Patent number
US07629357B2

Reaction notes

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