Hydrochloric Acid → HCID 178509303, compound

HRID 2388353Notes

Reaction equation

HRID 2388353 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]3[C:15](=[NH:16])[O:14][NH:13][C:12]3=[NH:17])[CH2:7][CH2:6]2)[O:4]CC1.Cl>C(#N)C>[NH:17]=[C:12]1[CH:11]([CH:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)[C:15](=[NH:16])[O:14][NH:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178509302HCID 178509302, compound

Product 1

HCID 178509303HCID 178509303, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(1,4-dioxa-spiro[4.5]dec-8-yl)-isoxazolidine-3,5-diylidenediamine (as prepared in the previous step, 0.078 g, 0.326 mmol) in acetonitrile (10 mL) was treated with 1N aqueous HCl (3.2 mL, 3.2 mmol), and stirred at ambient temperature for 6 h. After removing the MeCN in vacuo, the reaction was treated with saturated aqueous NaHCO3 (ca. 7 mL), stirred at ambient temperature overnight, and extracted thrice with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound as an orange gum.

Workup

  1. customAfter removing the MeCN in vacuo
  2. additionthe reaction was treated with saturated aqueous NaHCO3 (ca. 7 mL)
  3. stirringstirred at ambient temperature overnight
  4. extractionextracted thrice with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-370a310d0f084d2b85d0cd27605e93a7
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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