Dicyclohexylcarbodiimide → HCID 67038034, compound

HRID 604247Notes

Reaction equation

HRID 604247 reaction equation
O.O.[C:3]([O:7][C:8]([NH:10][C@H:11]([C:19]([OH:21])=O)[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[NH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[N:25]1([CH2:24][CH2:23][NH:22][C:19](=[O:21])[C@H:11]([CH2:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[NH:10][C:8]([O:7][C:3]([CH3:4])([CH3:5])[CH3:6])=[O:9])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 33944N-(2-Aminoethyl)piperidineHCID 27960291-Hydroxybenzotriazole hydrateHCID 66637966HCID 66637966, compound

Product 1

HCID 67038034HCID 67038034, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 200.5 mg of N-t-butoxycarbonyl-β-cyclohexyl-L-alanine dihydrate (0.652 mmol) in tetrahydrofuran (1.5 mL), 101.7 mg of 1-(aminoethyl)piperidine (0.793 mmol), 89.7 mg of 1-hydroxybenzotriazole hydrate (0.664 mmol), and 146.1 mg of N,N′-dicyclohexylcarbodiimide (0.708 mmol) were added with stirring under ice cooling. The reaction mixture was stirred for 1 hour under ice cooling and for 1 hour at room temperature, and then concentrated under reduced pressure. Ethyl acetate (1 mL) was added to the residue. Insoluble materials were removed by filtration, and then the filtrate was concentrated under reduced pressure. The residue (438 mg) was purified by column chromatography on alumina (alumina 2 g, chloroform), whereby 267 mg of the crude product was obtained. The crude product was purified by silica gel column chromatography [silica gel 10 g, about 15% ammonia/methanol-chloroform (1:100)], whereby 240.0 mg of N-t-butoxycarbonyl-β-cyclohexyl-L-alanine 2-(1-piperidinyl)ethyl amide was obtained as a colorless oil (yield 96%)

Workup

  1. stirringThe reaction mixture was stirred for 1 hour under ice cooling and for 1 hour at room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionEthyl acetate (1 mL) was added to the residue
  4. customInsoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue (438 mg) was purified by column chromatography on alumina (alumina 2 g, chloroform)
  7. customwhereby 267 mg of the crude product was obtained
  8. customThe crude product was purified by silica gel column chromatography [silica gel 10 g, about 15% ammonia/methanol-chloroform (1:100)]

Sources & evidence

ORD record
ord-5331bf26608e40d6a1e3a1044cb5cfcb
Source dataset
uspto-grants-2011_03
Patent number
US07910556B2

Reaction notes

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