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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → isopropyl 2-(3-(6-Hexyl-1-naphthamido)phenoxy)acetate

HRID 472783
Notes
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Reaction equation

HRID 472783 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[CH2:13]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25]([C:29]([OH:31])=O)=[CH:24][CH:23]=[CH:22]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:32][C:33]1[CH:34]=[C:35]([CH:44]=[CH:45][CH:46]=1)[O:36][CH2:37][C:38]([O:40][CH:41]([CH3:43])[CH3:42])=[O:39]>C(Cl)Cl>[CH2:13]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25]([C:29]([NH:32][C:33]1[CH:34]=[C:35]([CH:44]=[CH:45][CH:46]=1)[O:36][CH2:37][C:38]([O:40][CH:41]([CH3:42])[CH3:43])=[O:39])=[O:31])=[CH:24][CH:23]=[CH:22]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10608474Isopropyl 2-(3-aminophenoxy)acetateHCID 543973816-Hexyl-1-naphthoic acid

Product 1

HCID 66660445isopropyl 2-(3-(6-Hexyl-1-naphthamido)phenoxy)acetateYield 23.1%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

1-Ethyl-3-(3′-dimethylaminopropyl)-carbodiimide hydrochloride (EDCI, 157 mg) was added to a solution of 6-hexyl-1-naphthoic acid (161 mg, 0.63 mmol) and isopropyl 2-(3-aminophenoxy)acetate (131 mg, 0.63 mmol) in CH2Cl2 (6.3 mL) and the solution was stirred at room temperature overnight. The reaction was concentrated in vacuo, diluted with water (25 mL) and extracted with EtOAc (2×25 mL). The combined organic phase was washed with 1 N aqueous HCl (20 mL), saturated aqueous NaHCO3 (20 mL) and brine (20 mL), then dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified on 40 g silica (100% hexanes→100% EtOAc, gradient) to afford 65 mg (23%) of isopropyl 2-(3-(6-Hexyl-1-naphthamido)phenoxy)acetate.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with water (25 mL)
  3. extractionextracted with EtOAc (2×25 mL)
  4. washThe combined organic phase was washed with 1 N aqueous HCl (20 mL), saturated aqueous NaHCO3 (20 mL) and brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified on 40 g silica (100% hexanes→100% EtOAc, gradient)

Sources & evidence

ORD record
ord-04577eb0cbab4094956826a2102e533e
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08633220B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes