Sodium Iodide → 1-(Benzyl(methyl)carbamoyloxy)ethyl 5-(tetradecyloxy)furan-2-carboxylate

HRID 335536Notes

Reaction equation

HRID 335536 reaction equation
[CH2:1]([N:8]([CH3:15])[C:9](=[O:14])[O:10][CH:11](Cl)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([O:30][C:31]1[O:35][C:34]([C:36]([OH:38])=[O:37])=[CH:33][CH:32]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].O.O.O.O.O.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[I-].[Na+]>CN(C)C=O>[CH2:16]([O:30][C:31]1[O:35][C:34]([C:36]([O:38][CH:11]([O:10][C:9](=[O:14])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:15])[CH3:12])=[O:37])=[CH:33][CH:32]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 1151755-(Tetradecyloxy)-2-furoic acidHCID 668694551-Chloroethyl benzyl(methyl)carbamateHCID 86669148Tetrabutylammonium hydroxide pentahydrate

Product 1

HCID 498699001-(Benzyl(methyl)carbamoyloxy)ethyl 5-(tetradecyloxy)furan-2-carboxylateYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

The above prepared 1-chloroethyl benzyl(methyl)carbamate was dissolved in N,N-dimethylformamide (5 mL) and then 5-(tetradecyloxy)furan-2-carboxylic acid (0.180 g, 0.544 mmol), tetrabutylammonium hydroxide pentahydrate (0.209 g, 0.60 mmol), and sodium iodide (˜15 mg) were added to the reaction vessel. The resulting suspension was heated to 60° C. with stirring for 14 hrs. HPLC analysis of the reaction solution indicated that all of the starting material had been converted to a product of lower polarity. The reaction was then quenched with brine (5 mL), water (5 mL) and EtOAc (70 mL). The organic phase was 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 EtOAc in hexanes, 5-20% to yield 0.120 g (43%) of the title compound as a slightly brown oil. 1H NMR (300 MHz, CDCl3) δ: 7.15-7.40 (m, 6H), 7.05 (p, 1H), 5.30 (d, 1H), 4.40-4.60 (m, 2H), 4.10 (t, 2H), 2.85 (d, 3H) 1.7-1.9 (m, 2H), 1.79 (p, 2H), 1.55-1.62 (m, 3H), 1.18-1.50 (m, 22H), 0.89 (t, 3H).

Workup

  1. customThe reaction was then quenched with brine (5 mL), water (5 mL) and EtOAc (70 mL)
  2. washThe organic phase was washed successively with water (30 mL) and brine (30 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting crude material was purified by flash chromatography
  6. washeluting with EtOAc in hexanes, 5-20%

Sources & evidence

ORD record
ord-176c4937edeb4d71bce7a4c335b768e3
Source dataset
uspto-grants-2014_11
Patent number
US08884034B2

Reaction notes

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