1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 16749536, compound

HRID 1279856Notes

Reaction equation

HRID 1279856 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7][C@@H:8]([CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.O[NH:35][C:36](=[NH:44])[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1>ClCCl.CN(C)C1C=CN=CC=1>[CH:15]1([CH2:14][CH2:13][CH2:12][C@@H:8]([C:9]2[O:11][N:44]=[C:36]([CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=3)[N:35]=2)[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9835906(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acidHCID 178510813HCID 178510813, compound

Product 1

HCID 16749536HCID 16749536, compoundYield 25.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid (Preparation 1) (300 mg, 1.00 mmol) in dichloromethane (15 ml) was treated sequentially with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (192 mg, 1.00 mmol), 4-(dimethylamino)pyridine (125 mg, 1.02 mmol) and N-hydroxy-2-(2-pyridinyl)ethanimidamide (Chem.Pharm.Bull.; 21; 10; 1973; 2146-2160) (152 mg, 1.00 mmol). The resulting mixture was stirred at room temperature for 17 hours. The solvent was removed under reduced pressure and the residue was heated neat at 120° C. under a nitrogen atmosphere for 2 hours. The crude product was then purified by column chromatography on silica gel eluting with dichloromethane:methanol (99:1). The residue was further purified by column chromatography on silica gel eluting with ethyl acetate: pentane (30:70) to afford the title compound as an oil (107 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. temperaturethe residue was heated neat at 120° C. under a nitrogen atmosphere for 2 hours
  3. customThe crude product was then purified by column chromatography on silica gel eluting with dichloromethane:methanol (99:1)
  4. customThe residue was further purified by column chromatography on silica gel eluting with ethyl acetate: pentane (30:70)

Sources & evidence

ORD record
ord-2821d3fc3a7841609d67a4bd0687a8cf
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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