Triethylamine → HCID 21949151, compound

HRID 2376834Notes

Reaction equation

HRID 2376834 reaction equation
N1([NH:7][C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])CCNCC1.[OH:18][C:19]([CH3:24])([CH3:23])[C:20](O)=[O:21].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[CH2:48]([N:50](CC)[CH2:51][CH3:52])[CH3:49]>O1CCCC1>[OH:18][C:19]([CH3:24])([CH3:23])[C:20]([N:50]1[CH2:51][CH2:52][N:7]([C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9])[CH2:49][CH2:48]1)=[O:21]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 116712-Hydroxyisobutyric acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69316859HCID 69316859, compound

Product 1

HCID 21949151HCID 21949151, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl piperazine-1-carbamate (2.203 g, 10.0 mmol) was dissolved in tetrahydrofuran (50 ml); 2-hydroxy-2-methylpropionic acid (1.25 g, 12.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.30 g, 12.0 mmol), 1-hydroxy-1H-benzotriazole monohydrate (1.84 g, 12.0 mmol) and triethylamine (3.35 ml, 24.0 mmol) were added; and the reaction mixture was stirred at room temperature for 7 hours. The reaction mixture was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed with water, a saturated aqueous solution of sodium hydrogencarbonate and brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and dried under reduced pressure to yield the title compound (2.823 g, 9.21 mmol, 92.1%) as a colorless oil.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and 1N hydrochloric acid
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and brine, and dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-3255af95b5c14c1c8c43d28e9eb4530c
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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