1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 131734746, compound

HRID 1775766Notes

Reaction equation

HRID 1775766 reaction equation
[C:1]([O:5][C:6](/[C:8](=[CH:15]\[C:16](\[CH3:31])=[CH:17]\[CH:18]([CH3:30])[CH2:19][CH:20]([CH3:29])[CH2:21][CH:22]([CH3:28])[CH2:23][CH:24]([CH3:27])[CH2:25][CH3:26])/[CH2:9][CH:10]([CH3:14])[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.ClCCl>[CH3:14][CH:10]([CH2:9]/[C:8](=[CH:15]/[C:16](/[CH3:31])=[CH:17]/[CH:18]([CH3:30])[CH2:19][CH:20]([CH3:29])[CH2:21][CH:22]([CH3:28])[CH2:23][CH:24]([CH3:27])[CH2:25][CH3:26])/[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:11]([O:13][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:12]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11815394Tert-butyl 2-hydroxyacetateHCID 118035475HCID 118035475, compound

Product 1

HCID 131734746HCID 131734746, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(Step 1) To Compound 8 (16 mg, 0.037 mmol), dichloromethane (1.8 mL), tert-butyl 2-hydroxyacetate (5.8 mg, 0.044 mmol), EDC.HCl (10.5 mg, 0.055 mmol), and DMAP (0.4 mg, 0.0037 mmol) were added, and the resulting mixture was stirred at room temperature for 4 days. The solvent was evaporated under reduced pressure, and the resulting residue was purified by thin-layer column chromatography (ethyl acetate/n-hexane=1/9), whereby 1-(2-tert-butoxy-2-oxoethyl) 5-tert-butyl (Z)-2-methyl-4-{(E)-2,4,6,8,10-pentamethyldodec-2-enylidene}pentanedioate (14.7 mg, 73%) was obtained.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe resulting residue was purified by thin-layer column chromatography (ethyl acetate/n-hexane=1/9)

Sources & evidence

ORD record
ord-c9d6ad3684bd4b68aa81284dce7e1cc8
Source dataset
uspto-grants-2016_02
Patent number
US09260459B2

Reaction notes

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