Sodium Iodide → 2-(Benzyl(methyl)amino)-2-oxoethyl 5-(tetradecyloxy)furan-2-carboxylate

HRID 335541

Reaction equation

HRID 335541 reaction equation
[CH2:1]([N:8]([CH3:13])[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([O:28][C:29]1[O:33][C:32]([C:34]([OH:36])=[O:35])=[CH:31][CH:30]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].O.O.O.O.O.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[I-].[Na+]>CN(C)C=O>[CH2:14]([O:28][C:29]1[O:33][C:32]([C:34]([O:36][CH2:10][C:9]([N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:13])=[O:12])=[O:35])=[CH:31][CH:30]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 1151755-(Tetradecyloxy)-2-furoic acidHCID 4639192N-benzyl-2-chloro-N-methylacetamideHCID 86669148Tetrabutylammonium hydroxide pentahydrate

Product 1

HCID 498701662-(Benzyl(methyl)amino)-2-oxoethyl 5-(tetradecyloxy)furan-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

The above prepared N-benzyl-2-chloro-N-methylacetamide (0.250 g) was dissolved in 10 mL of N,N-dimethylformamide. To this solution were added 5-(tetradecyloxy)furan-2-carboxylic acid (0.180 g, 0.544 mmol), tetrabutylammonium hydroxide pentahydrate (0.209 g, 0.554 mmol), and sodium iodide (˜15 mg). The suspension was heated to 60° C. with stirring for 14 hrs. The reaction was quenched with brine (5 mL), water (5 mL) and EtOAc (40 mL). The phases were separated and the organic phase was further diluted with EtOAc (30 mL), washed successively with water (30 mL) and brine (30 mL) and then dried and concentrated. The resulting crude material was purified by flash chromatography eluting with 5-20% EtOAc in hexanes to give the desired compound as a viscous oil. The material was further purified by recrystallization from 2-propanol and water to yield 0.130 g (52%) of the title compound. 1H NMR (300 MHz, CDCl3) δ: 7.20-7.40 (m, 6H), 5.30-5.35 (m, 1H), 4.92 (s, 2H), 4.50-4.61 (app d, 2H), 4.10 (m, 2H), 2.90-2.98 (app d, 3H), 1.79 (p, 2H), 1.18-1.50 (m, 22H), 0.89 (t, 3H).

Workup

  1. customThe reaction was quenched with brine (5 mL), water (5 mL) and EtOAc (40 mL)
  2. customThe phases were separated
  3. additionthe organic phase was further diluted with EtOAc (30 mL)
  4. washwashed successively with water (30 mL) and brine (30 mL)
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting crude material was purified by flash chromatography
  8. washeluting with 5-20% EtOAc in hexanes

Sources & evidence

ORD record
ord-5c605813c70442d6bd8a1fee70702c12
Source dataset
uspto-grants-2014_11
Patent number
US08884034B2

Linked notes

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