Oxalic Acid → HCID 70279186, compound

HRID 1655105Notes

Reaction equation

HRID 1655105 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH3:7][C:8]1[CH:12]=[C:11]([C@H:13]2[CH2:17][C@H:16]([OH:18])[CH2:15][N:14]2[CH3:19])[O:10][N:9]=1>C(OCC)C>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH3:7][C:8]1[CH:12]=[C:11]([C@H:13]2[CH2:17][C@H:16]([OH:18])[CH2:15][N:14]2[CH3:19])[O:10][N:9]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 15294392HCID 15294392, compound

Product 1

HCID 70279186HCID 70279186, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of oxalic acid (13.6 mg, 0.151 mmol) in diethyl ether was added dropwise to a stirring solution of 3-methyl-5-(trans-4-hydroxy-1-methyl-2-pyrrolidinyl)-isoxazole (21 e, 25.0 mg, 0.14 mmol) in diethyl ether. After 30 minutes of stirring at ambient temperature, the resulting precipitate was filtered and washed with diethyl ether three times to give, after evaporation of the solvents in vacuo., 26.0 mg of the title compound (21). M.P. 125°-126° C. MS (DCl/NH3) m/e 183 (M+H)+, 200 (M+NH4)+. 1H NMR (D2O) δ: 6.67 (s, 1H, ArH), 5.07-5.17 (m, 1H, OCH), 4.82 (dd, J=10.5 Hz, J=9.9 Hz, 1H, ArCHN), 3.93-4.03 (m, 1H, NCHH), 3.34-3.43 (m, 1H, NCHH), 2.98 (s, 3H, NCH3), 2.66 (ddd, J= 14.4 Hz, J=10.5 Hz, J=4.8 Hz, 1H, OCCHH), 2.55 (dddd, J=14.4 Hz, J=9.9 Hz, J=1.8 Hz, J=1.8 Hz, 1H, OCCHH), 2.33 (s, 3H, ARCH3). Anal. calcd. for C11H16N26lO6 : C, 48.53; H, 5.88; N, 10.29. Found: C, 48.58; H, 5.83; N, 10.04.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with diethyl ether three times
  3. customto give
  4. customafter evaporation of the solvents in vacuo

Sources & evidence

ORD record
ord-0e1e7d71261748339d800582e1138aa8
Source dataset
uspto-grants-1995_04
Patent number
US05409946

Reaction notes

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