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Dihexylamine → N-t-butoxycarbonyl-(2-cyanophenyl)alanine dihexylamide

HRID 651582
Notes
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Reaction equation

HRID 651582 reaction equation
[C:1]([O:5][C:6]([N:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]#[N:21])[C@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[CH2:29]([N:28]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:11](=[O:13])[C@H:9]([CH3:10])[N:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]#[N:21])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8920DihexylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 54403898N-t-butoxycarbonyl-(2-cyanophenyl)alanine

Product 1

HCID 53745284N-t-butoxycarbonyl-(2-cyanophenyl)alanine dihexylamideYield 79.1%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.81 g of the crude N-t-butoxycarbonyl-(2-cyanophenyl)alanine and 0.67 g of dihexylamine in 8 ml of N,N-dimethylformamide were added 0.55 g of 1-hydroxybenzotriazole monohydrate and 0.69 g of N-ethyl-N′-dimethylaminopropylcarbodiimide hydrochloride, followed by stirring at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with 5% aqueous potassium bisulfate solution, a saturated aqueous sodium bicarbonate solution and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica gel; Wakogel C200 (manufactured by Wako Pure Chemicals), developing solvent; hexane-ethyl acetate=4:1) to give 1.01 g of N-t-butoxycarbonyl-(2-cyanophenyl)alanine dihexylamide.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 5% aqueous potassium bisulfate solution
  3. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  4. customAfter removal of the drying agent
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by chromatography (silica gel; Wakogel C200 (manufactured by Wako Pure Chemicals), developing solvent; hexane-ethyl acetate=4:1)

Sources & evidence

ORD record
ord-a6e5263d093541fdac799a430c8cc3e1
Source dataset
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06281355B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes