Acetamidomalonic acid diethyl ester → HCID 21849210, compound

HRID 1451608Notes

Reaction equation

HRID 1451608 reaction equation
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[O-]CC.[Na+].Br[CH2:21][CH2:22][CH2:23][S:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].Cl.C(O)C>C(O)C>[C:1]([NH:4][C:5]([CH2:21][CH2:22][CH2:23][S:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 14041Acetamidomalonic acid diethyl esterHCID 2723922Sodium ethoxideHCID 21887872Ethanol hydrochlorideHCID 86750380HCID 86750380, compound

Product 1

HCID 21849210HCID 21849210, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl acetamidomalonate (1.6 g) was dissolved in 30 ml of dehydrated ethanol and 505 mg of sodium ethoxide and 2 g of 3-bromopropyldodecyl sulfide were added thereto. The mixture was refluxed under a nitrogen atmosphere overnight. The reaction mixture was neutralized with concentrated hydrochloric acid-ethanol (1:11) and concentrated. The concentrate was purified by silica gel column chromatography using hexane-ethyl acetate (5:1→5:2) as an eluent to give 1.722 g of colorless, powdery diethyl 2-acetamido-2-(3-dodecylthiopropyl)malonate. IRν max (CHCl3): 3440, 2930, 2850, 1740, 1680, 1500, 1380, 1260, 1100, 1020, 860 cm-1 1 H-NMR (CDCl3 /TMS) δ: 0.88 (3H, t, J=7.4 Hz), 1.26 (18H, m), 1.26 (6H, t, J=7.3 Hz), 1.57 (4H, m), 2.04 (3H, s), 2.42 (2H, m), 2.47 (2H, t, J=7.3 Hz), 2.48 (2H, t, J=7.3 Hz), 4.25 (4H, q, J=7.4 Hz), 6.78 (1H, s)

Workup

  1. temperatureThe mixture was refluxed under a nitrogen atmosphere overnight
  2. concentrationconcentrated
  3. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-327c186d028c41c2b5533d908e97490b
Source dataset
uspto-grants-1997_02
Patent number
US05604229

Reaction notes

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