Methyl iodide → HCID 178456813, compound

HRID 2273030Notes

Reaction equation

HRID 2273030 reaction equation
[NH2:1][CH:2]1[CH:7]([O:8][CH2:9]C2C=CC=CC=2)[CH:6](OCC2C=CC=CC=2)[CH:5]([CH2:24][O:25]CC2C=CC=CC=2)[CH2:4][CH:3]1[OH:33].[CH2:34]([N:37]=C=S)[CH2:35][CH3:36].CI.C([O-])(O)=[O:43].[Na+]>C1COCC1>[OH:25][CH2:24][CH:5]1[CH:4]([OH:43])[CH:3]([OH:33])[CH:2]2[N:1]=[C:9]([NH:37][CH2:34][CH2:35][CH3:36])[O:8][CH:7]2[CH2:6]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 69403Propyl IsothiocyanateHCID 516892Sodium BicarbonateHCID 67480625HCID 67480625, compound

Product 1

HCID 178456813HCID 178456813, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Intermediate B (151 mg, 0.338 mmol) in dry THF (4 mL) was added a solution of propyl isothiocyanate (42.6 mg, 0.422 mmol) in dry THF (1 mL). The mixture was stirred at room temperature for 16 h. Solvents were evaporated under reduced pressure. The residue was dissolved in acetone (3 mL). MeI (96 mg, 0.676 mmol) was added. The mixture was stirred at room temperature for 5 h. Satd. aqueous NaHCO3 (2 mL) was added and stirred at room temperature for 10 min. The mixture was further diluted with satd. aqueous NaHCO3 (20 mL), extracted with EtOAc (2×15 mL). The combined extracts were washed with brine and dried over Na2SO4. Solvents were evaporated under reduced pressure. The crude product was purified by silica gel column chromatography, eluted with 96:3:1 EtOAc-MeOH—NH4OH (28% aqueous) to give the aminooxazoline (112 mg, 64%) as a syrup. 1H NMR (400 MHz, CDCl3) δ 7.38-7.24 (m, 15H), 4.84 (d, J=11.5 Hz, 1H), 4.79-4.75 (m, 1H), 4.77 (d, J=11.2 Hz, 1H), 4.69 (d, J=11.5 Hz, 1H), 4.45 (d, J=11.2 Hz, 1H), 4.45 (s, 2H), 4.05 (dd, J=7.9, 5.4 Hz, 1H), 3.64 (t, J=5.9 Hz, 1H), 3.56 (dd, J=9.0, 5.2 Hz, 1H), 3.52-3.46 (m, 2H), 3.21-3.08 (m, 2H), 2.17 (dt, J=14.9, 3.4 Hz, 1H), 2.05-1.98 (m, 1H), 1.87 (ddd, J=15.4, 12.1, 3.7 Hz, 1H), 1.54 (sextuplet, J=7.3 Hz, 2H), 0.91 (t, J=7.4 Hz, 3H).

Workup

  1. customSolvents were evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in acetone (3 mL)
  3. stirringThe mixture was stirred at room temperature for 5 h
  4. stirringstirred at room temperature for 10 min
  5. additionThe mixture was further diluted with satd
  6. extractionaqueous NaHCO3 (20 mL), extracted with EtOAc (2×15 mL)
  7. washThe combined extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. customSolvents were evaporated under reduced pressure
  10. customThe crude product was purified by silica gel column chromatography
  11. washeluted with 96:3:1 EtOAc-MeOH—NH4OH (28% aqueous)

Sources & evidence

ORD record
ord-e49a6eeaecc0442096a5163d538a5f6f
Source dataset
uspto-grants-2015_09
Patent number
US09120781B2

Reaction notes

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