Diethyl Oxalate → HCID 67243377, compound

HRID 729258Notes

Reaction equation

HRID 729258 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][S:6]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])=[O:7].[C:16](OCC)(=[O:22])[C:17](OCC)=[O:18].CC(C)([O-])C.[K+]>CN(C=O)C>[OH:22][C:16]1[C:17](=[O:18])[N:5]([CH2:4][CH2:3][O:2][CH3:1])[S:6](=[O:7])(=[O:8])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 4467329N-(2-methoxyethyl)-1-phenylmethanesulfonamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 67243377HCID 67243377, compoundYield 6.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(2-methoxyethyl)-1-phenylmethanesulfonamide (3.5 g, 14.5 mmol) and diethyl oxalate (2.33 g, 16.0 mmol) in dry DMF was cooled in an ice-bath. Potassium tert-butoxide (2.17 g, 18.4 mmol) was added and after 5 min the ice-bath was removed and the reaction was stirred at rt for 22 h. HCl (2M, 45 mL) was added to the mixture and the acidic solution was extracted 3 times with DCM. The combined organic layer was washed 4 times with water, dried through a phase separator and evaporated. The residue was purified by preparative HPLC [0.1M N OAc/MeCN, gradient A:B (9:1 to 1:9)] to give the title compound (0.250 g, 6%) as a solid; 1H NMR (500 MHz, CD3OD): δ 7.90-7.94 (m, 2H), 7.28-7.33 (m, 2H), 7.10-7.15 (m, 1H), 3.79 (t, 2H), 3.68 (t, 2H), 3.34 (s, 3H); Mass Spectrum: M−H+ 282.

Workup

  1. customwas removed
  2. additionHCl (2M, 45 mL) was added to the mixture
  3. extractionthe acidic solution was extracted 3 times with DCM
  4. washThe combined organic layer was washed 4 times with water
  5. customdried through a phase separator
  6. customevaporated
  7. customThe residue was purified by preparative HPLC [0.1M N OAc/MeCN, gradient A:B (9:1 to 1:9)]

Sources & evidence

ORD record
ord-1b86e9767d8449e5a154d4d65d87c66c
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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