Acetonitrile → HCID 70689323, compound

HRID 1477102Notes

Reaction equation

HRID 1477102 reaction equation
[C@H:1]([OH:14])([C@H:9]([OH:13])[C:10]([OH:12])=[O:11])[C@H:2]([OH:8])[C@@H:3]([OH:7])[C:4]([OH:6])=[O:5].[CH3:15][CH:16]([NH:23][CH3:24])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21].CC#N>O.CCOCC.CO>[CH3:15][CH:16]([NH:23][CH3:24])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21].[C@H:1]([OH:14])([C@H:9]([OH:13])[C:10]([OH:12])=[O:11])[C@H:2]([OH:8])[C@@H:3]([OH:7])[C:4]([OH:6])=[O:5].[C@H:1]([OH:14])([C@H:9]([OH:13])[C:10]([OH:12])=[O:11])[C@H:2]([OH:8])[C@@H:3]([OH:7])[C:4]([OH:6])=[O:5]

Participants

7

Reactant 3

HCID 6342AcetonitrileHCID 22297IsomethepteneHCID 3037582Galactaric acid3×

Product 1

HCID 70689323HCID 70689323, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Mucic acid (628 mg, 3.0 mmol) was suspended in distilled water (40 mL) at room temperature (RT). Isometheptene-isomer-2 (3.04 g, 21.5 mmol) was dissolved in Et2O (57 mL) and added dropwise via addition funnel to the mucic acid at RT while stirring to give dissolution of the mucic acid suspension. The biphasic solution was stirred at RT for 16 h, the aqueous layer was separated, extracted with toluene (5×80 mL) (the final extraction with toluene was stood for 30 min before the aqueous layer was separated), then the aqueous layer was evaporated in vacuo (1 mm Hg) at 35°-40° C. to give a white solid which was dissolved in MeOH (8 mL) by gently heating to give a solution. CH3CN (80 mL) was added slowly dropwise via addition funnel at RT to the stirred MeOH solution to give a suspension which was stirred at RT for about 30 min. The solids were filtered, washed with CH3CN thrice, air-dried, then dried in vacuo (0.1 mm Hg) at RT for 16 h to give the titled compound as a white (1.390 mg, 70%). The molar ratio of Isometheptene to mucic acid in the salt was 2:1, based on the NMR spectrum: 1H NMR (500 MHz, in D2O), 1H NNMR in CDCl3: 5.16 ppm 1 Ht (J=6.8 Hz), 4.25 ppm 1 Hs, 3.95 ppm 1 Hs, 3.2 ppm 1 Hm, 2.66 ppm 3 Hs, 2.09 ppm 2 Hm, 1.75 ppm 1 Hm, 1.69 ppm 3 Hs, 1.62 ppm 3 Hs, 1.58 ppm 1 Hm, 1.29 ppm 3 Hd (J=7 Hz). MS: mass calc for C9H19N, 141.15. Found: 142.4 (M+H).

Workup

  1. custom(RT)
  2. customto give
  3. stirringThe biphasic solution was stirred at RT for 16 h
  4. customthe aqueous layer was separated
  5. extractionextracted with toluene (5×80 mL) (the final
  6. extractionextraction with toluene
  7. customwas separated), then the aqueous layer
  8. customwas evaporated in vacuo (1 mm Hg) at 35°-40° C.
  9. customto give a white solid which
  10. temperatureby gently heating
  11. customto give a solution
  12. customto give a suspension which
  13. stirringwas stirred at RT for about 30 min
  14. filtrationThe solids were filtered
  15. washwashed with CH3CN thrice
  16. customair-dried
  17. customdried in vacuo (0.1 mm Hg) at RT for 16 h

Sources & evidence

ORD record
ord-fa21520c085b49d89345e19bfa882f30
Source dataset
uspto-grants-2016_08
Patent number
US09403755B2

Reaction notes

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