Hydrochloric Acid → HCID 23103542, compound

HRID 230929Notes

Reaction equation

HRID 230929 reaction equation
C(OC([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([O-])=[O:11])=O)(C)(C)C.[CH2:15]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.ON1C2C=CC=CC=2N=N1.[ClH:41].C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O.C(N(CC)CC)C>[ClH:41].[NH2:8][C:9]([CH3:14])([CH3:13])[C:10]([N:28]1[CH2:29][CH2:30][N:25]([C:23]([O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:24])[CH2:26][CH2:27]1)=[O:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 643495Benzyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7004985HCID 7004985, compound

Product 1

HCID 23103542HCID 23103542, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)-2-methylpropionate (4.06 g) in N,N-dimethylformamide (40 mL) were added 1-(benzyloxycarbonyl)piperazine (6.6 g), 1-hydroxybenzotriazole (3.24 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (7.67 g) and triethylamine (11.2 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, 1 mol/L aqueous sodium hydroxide solution, water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue was added 4 mol/L hydrochloric acid (1,4-dioxane solution, 25 mL), and the mixture was stirred at room temperature for 4 hours. To the reaction mixture was added diethyl ether (50 mL), and the insoluble material was collected by filtration. The collected solid was washed with diethyl ether and dried under reduced pressure to give the title compound (4.65 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with water, 1 mol/L aqueous sodium hydroxide solution, water and brine successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. additionTo the residue was added 4 mol/L hydrochloric acid (1,4-dioxane solution, 25 mL)
  6. stirringthe mixture was stirred at room temperature for 4 hours
  7. additionTo the reaction mixture was added diethyl ether (50 mL)
  8. filtrationthe insoluble material was collected by filtration
  9. washThe collected solid was washed with diethyl ether
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-98c61b32b2014508951e69474095d4ab
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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