Hydrochloric Acid → HCID 178523389, compound

HRID 411655Notes

Reaction equation

HRID 411655 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.C([O-])([O-])=O.[K+].[K+].[CH2:18]([O:25][C:26](Cl)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>O.O1CCOCC1>[CH2:18]([O:25][C:26]([NH:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]1)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 178511262HCID 178511262, compound

Product 1

HCID 178523389HCID 178523389, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A 1L 3-neck flask was charged with 25.09 (160 mmol) trans-4-aminomethyl-cyclohexanecarboxylic acid, 77.4 g (560 mmol) K2CO3, 250 mL dioxane and 250 mL water. The suspension was stirred, then 28.5 mL (200 mmol) benzylchloroformate was added dropwise. The reaction mixture was then stirred at room temperature for 6.5 hours then poured into 800 mL water and acidified (slowly) with 1N HCl. The resulting white precipitate was filtered and dried-45.6 g.

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for 6.5 hours
  2. filtrationThe resulting white precipitate was filtered
  3. customdried-45.6 g

Sources & evidence

ORD record
ord-93296869d58649a3bf8c244ff098b6df
Source dataset
uspto-grants-2003_05
Patent number
US06559168B2

Reaction notes

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