Acetonitrile → HCID 70689323, compound

HRID 1477097Notes

Reaction equation

HRID 1477097 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, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Mucic acid (840 mg, 4.0 mmol) was suspended in distilled water (40 mL) at RT. Isometheptene-isomer-1 (1.356 g, 9.6 mmol) was dissolved in Et2O (19 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 solid (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. customto give
  2. stirringThe biphasic solution was stirred at RT for 16 h
  3. customthe aqueous layer was separated
  4. extractionextracted with toluene (5×80 mL) (the final
  5. extractionextraction with toluene
  6. customwas separated), then the aqueous layer
  7. customwas evaporated in vacuo (1 mm Hg) at 35°-40° C.
  8. customto give a white solid which
  9. temperatureby gently heating
  10. customto give a solution
  11. customto give a suspension which
  12. stirringwas stirred at RT for about 30 min
  13. filtrationThe solids were filtered
  14. washwashed with CH3CN thrice
  15. customair-dried
  16. customdried in vacuo (0.1 mm Hg) at RT for 16 h

Sources & evidence

ORD record
ord-ff45871f803b4cd18a4ce8a4eca9eb4b
Source dataset
uspto-grants-2016_08
Patent number
US09403755B2

Reaction notes

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