Hydrochloric Acid → HCID 178511300, compound

HRID 1485113Notes

Reaction equation

HRID 1485113 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C@H:7]2[CH2:10][C@H:9]([CH2:11][NH:12]C(=O)OC(C)(C)C)[CH2:8]2)=[CH:4][CH:3]=1.Cl.C(OCC)C>O1CCOCC1>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C@H:7]2[CH2:10][C@H:9]([CH2:11][NH2:12])[CH2:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 178453657HCID 178453657, compound

Product 1

HCID 178511300HCID 178511300, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution in 1,4-dioxane (30 mL) of the compound (0.98 g) obtained in step (5) above, a solution (25 mL) of 4 mol/L hydrogen chloride in 1,4-dioxane was added and the mixture was stirred at room temperature for 5 hours. After adding diethyl ether (120 mL), the mixture was stirred for another two hours and thereafter the precipitate was recovered by filtration. The recovered precipitate was dissolved in an aqueous solution of 1 mol/L sodium hydroxide and chloroform and two extractions were conducted with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate and the desiccant was removed by filtration. The filtrate was concentrated under reduced pressure to give the titled compound as a colorless oil (660 mg).

Workup

  1. stirringthe mixture was stirred for another two hours
  2. filtrationthe precipitate was recovered by filtration
  3. dissolutionThe recovered precipitate was dissolved in an aqueous solution of 1 mol/L sodium hydroxide and chloroform and two extractions
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. customthe desiccant was removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b6ad57eebbba4f51a9a5ff61708b04f8
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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