Hydrochloric Acid → HCID 28343697, compound

HRID 2041474Notes

Reaction equation

HRID 2041474 reaction equation
Cl.C(OC([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])=[CH:13][CH:12]=1)=O)(C)(C)C>O1CCOCC1.ClCCl>[CH:19]1([C:17]([C:14]2[CH:15]=[CH:16][C:11]([CH2:10][NH2:9])=[CH:12][CH:13]=2)=[O:18])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57656154HCID 57656154, compound

Product 1

HCID 28343697HCID 28343697, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 4N hydrogen chloride in dioxane (1 mL) to a stirred solution of N-(tert-butoxycarbonyl)-4-cyclohexanecarbonyl-benzylamine (197 mg, 0.621 mmol) in anhydrous dichloromethane (4 mL) and stir the mixture at ambient temperature for 16 h. Concentrate in vacuo and partition the residue between dichloromethane and saturated aqueous NaHCO3. Extract the aqueous phase twice with dichloromethane. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to give the title compound (125 mg, 93%) that was used without any further purification. MS (ES+) m/z: 218 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. custompartition the residue between dichloromethane and saturated aqueous NaHCO3
  3. extractionExtract the aqueous phase twice with dichloromethane
  4. dry with materialDry the combined organic extracts over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-bae8eede1f504d03a3f822d55a276a19
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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