Hydrochloric Acid → HCID 86699521, compound

HRID 571612Notes

Reaction equation

HRID 571612 reaction equation
C(OC([N:8]([CH2:29][CH:30]1[CH2:32][CH2:31]1)/[N:9]=[C:10](\[S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=O)(C)(C)C.Cl.C(=O)([O-])O.[Na+]>O1CCOCC1>[CH:30]1([CH2:29][NH:8]/[N:9]=[C:10](/[S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])\[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:32][CH2:31]1.[CH:30]1([CH2:29][NH:8]/[N:9]=[C:10](\[S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])/[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:32][CH2:31]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 140619947HCID 140619947, compound

Product 2

HCID 86699521HCID 86699521, compoundYield 17%HCID 86699522HCID 86699522, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of Z-ethyl 2-(2-t-butoxycarbonyl-2-(cyclopropylmethyl)hydrazono)-2-(dodecylthio)acetate (10.0 g, 21.3 mmol) in dioxane (10 ml) was added a 4M solution of hydrogen chloride in dioxane (10 ml), and stirred at room temperature for 2 hours. The reaction solution was added to saturated aqueous sodium hydrogen carbonate solution, and extracted with tert-butyl methyl ether 2 times. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 1.26 g of E-ethyl 2-(2-(cyclopropylmethyl)hydrazono)-2-(dodecylthio)acetate (yield: 16%) and 1.34 g of Z-ethyl 2-(2-(cyclopropylmethyl)hydrazono)-2-(dodecylthio)acetate (yield: 17%).

Workup

  1. extractionextracted with tert-butyl methyl ether 2 times
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-8e1b59d317574becb9ff7210da596542
Source dataset
uspto-grants-2015_05
Patent number
US09029295B2

Reaction notes

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