Ethyl Acetate → HCID 59615978, compound

HRID 1950754Notes

Reaction equation

HRID 1950754 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:18]=[C:19]([CH2:21][OH:22])[CH:20]=1)[O:6][CH2:7][CH2:8][N:9]([CH3:17])[C:10](=[O:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14].[CH3:23][Si](C=[N+]=[N-])(C)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>CO.C(O)(=O)C>[CH3:23][O:14][C:13](=[O:15])[CH2:12][CH2:11][C:10]([N:9]([CH2:8][CH2:7][O:6][C:5]1[CH:4]=[C:3]([CH2:2][OH:1])[CH:20]=[C:19]([CH2:21][OH:22])[CH:18]=1)[CH3:17])=[O:16]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 167693TrimethylsilyldiazomethaneHCID 516892Sodium BicarbonateHCID 59615929HCID 59615929, compound

Product 1

HCID 59615978HCID 59615978, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a cooled (0° C.) solution of N-[2-(3,5-Bis-hydroxymethyl-phenoxy)-ethyl]-N-methyl-succinamic acid (225 mg) in methanol (1 mL), was added (trimethylsilyl)diazomethane 2M in hexanes (840 μL) until persistence of the yellow colour. After 40 min, ethyl acetate (5 mL) and acetic acid (50 μL) were added, then, one minute later, a saturated aqueous solution of sodium hydrogen carbonate until pH=7. The aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Merck SuperVarioFlash 25 g column, Si60 15-40 μm), using gradient elution with a mixture of DCM (A)/MeOH (B), (gradient: 98% A: 2% B down to 90% A: 10% B) to give N-[2-(3,5-Bis-hydroxymethyl-phenoxy)-ethyl]-N-methyl-succinamic acid methyl ester (103 mg). LC/MS (Method A3): ES: m/z 348 (M+Na)+; m/z 326 (M+H)+ m/z 308 (M−H2O+H)+; RT=0.43 min

Workup

  1. customone minute
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washThe combined organic layers were washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo to a residue
  6. customThe residue was purified by silica gel chromatography (Merck SuperVarioFlash 25 g column, Si60 15-40 μm)
  7. washelution
  8. additionwith a mixture of DCM (A)/MeOH (B), (gradient: 98% A: 2% B down to 90% A: 10% B)

Sources & evidence

ORD record
ord-29d80cea1cc04c69bbd7e3f5673f0566
Source dataset
uspto-grants-2013_03
Patent number
US08404678B2

Reaction notes

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