Trifluoromethanesulfonic acid → Methyl (3R)-3-(benzyloxy)tetradecanoate

HRID 1022287Notes

Reaction equation

HRID 1022287 reaction equation
[OH:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([O:6][CH3:7])=[O:5].ClC(Cl)(Cl)C(=N)O[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.FC(F)(F)S(O)(=O)=O>C(Cl)Cl>[CH2:23]([O:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([O:6][CH3:7])=[O:5])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 98349453R-hydroxymyristic acid methyl ester

Product 1

HCID 13817922Methyl (3R)-3-(benzyloxy)tetradecanoateYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 30 (2.8 g, 10.83 mmol) and benzyl trichloroacetimidate (3.4 g, 14 mmol) in DCM (100 mL) was added trifluoromethanesulfonic acid (0.24 mL, 2.7 mmol) dropwise at 0° C. The resulting mixture was stirred at 0° C. for 6 h and warmed to room temperature. The mixture was washed with a saturated solution of NaHCO3 (300 mL) and water (300 mL) and the organic layer dried over Na2SO4. The drying agent was removed by filtration, and the solvents removed using a rotary evaporator. The residue was purified by chromatography on silica gel (80 g RediSep column, eluting with a gradient of 0% through 30% ethyl acetate/hexanes over 60 min, 60 mL/min) to give the product 31 (1.2 g, 32%) as a colorless liquid. 1H NMR (300 MHz, CDCl3) δ 7.30-7.05 (m, 5H), 4.51 (s, 2H), 3.90-3.80 (m, 1H), 3.70 (s, 3H), 2.58-2.45 (m, 2H), 1.80-1.60 (m, 2H), 1.50-1.20 (m, 18H), 0.85 (t, J=5.8 Hz, 3H).

Workup

  1. temperaturewarmed to room temperature
  2. washThe mixture was washed with a saturated solution of NaHCO3 (300 mL) and water (300 mL)
  3. dry with materialthe organic layer dried over Na2SO4
  4. customThe drying agent was removed by filtration
  5. customthe solvents removed
  6. customa rotary evaporator
  7. customThe residue was purified by chromatography on silica gel (80 g RediSep column
  8. washeluting with a gradient of 0% through 30% ethyl acetate/hexanes over 60 min

Sources & evidence

ORD record
ord-121c357316c84a0eaff517edef61c988
Source dataset
uspto-grants-2014_05
Patent number
US08722064B2

Reaction notes

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