Hydrochloric Acid → HCID 59504856, compound

HRID 1517208Notes

Reaction equation

HRID 1517208 reaction equation
Cl.C([Si](C)(C)[O:7][C@@H:8]1[CH2:12][N:11]=[C:10]([NH:13][CH2:14][CH:15](OCC)OCC)[CH2:9]1)(C)(C)C>O1CCOCC1>[N:13]1[CH:14]=[CH:15][N:11]2[CH2:12][C@@H:8]([OH:7])[CH2:9][C:10]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67356528HCID 67356528, compound

Product 1

HCID 59504856HCID 59504856, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

An aqueous solution of hydrochloric acid (0.625 M, 1000 mL) was added to a mixture of the compound isolated in Step 3 (207 g, 0.625 mol) in 1,4-dioxane (200 mL). The mixture was refluxed for 2 hours, and then cooled to room temperature, before washing with diethyl ether (3×300 mL). The aqueous layer was basified with sodium carbonate and extracted with dichloromethane (20×500 mL). The combined organic extracts were washed with brine (500 mL) evaporated under reduced pressure to give the title compound as a solid (55.5 gm 71%). 1H NMR (400 MHz, (CD3)2SO): δ 2.45 (m, 1H), 2.90 (m, 1H), 3.60 (m, 1H), 4.00 (m, 1H), 4.75 (m, 1H), 5.40 (m, 1H), 6.75 (m, 1H), 6.95 (m, 1H).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. washbefore washing with diethyl ether (3×300 mL)
  3. extractionextracted with dichloromethane (20×500 mL)
  4. washThe combined organic extracts were washed with brine (500 mL)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d446fbb95b484fe892c968d07870d653
Source dataset
uspto-grants-2012_07
Patent number
US08232269B2

Reaction notes

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