Cyclohexylamine → HCID 44332590, compound

HRID 412619Notes

Reaction equation

HRID 412619 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O[N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2N=N1.C1(N)CCCCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH2:12][C:13](=[O:15])[NH:18][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7965CyclohexylamineHCID 14349BenzyloxycarbonylglycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 44332590HCID 44332590, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(benzyloxycarbonyl)glycine (13.21 g), 1-hydroxybenzotriazole hydrate (9.39 g) in dimethylformamide (92 ml) were added cyclohexylamine (7.95 ml) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (13.32 g), and the mixture was stirred at room temperature for 7 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and washed successively with water, aqueous sodium hydrogencarbonate solution, 10% hydrochloric acid and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The obtained residue was recrystallized from ethyl acetate and hexane to give the title compound (16.799 g).

Workup

  1. customAfter completion of the reaction
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washwashed successively with water, aqueous sodium hydrogencarbonate solution, 10% hydrochloric acid and saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-0e45aebfa44045bf86015a61ace56d4a
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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