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

HRID 57218Notes

Reaction equation

HRID 57218 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-70760ca32e1a4b63b9ba85664c148196
Source dataset
uspto-grants-2016_09
Patent number
US09434718B2

Reaction notes

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