Dicyclohexylcarbodiimide → N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-3-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-hydroxy-methyl]-benzamide

HRID 2244037Notes

Reaction equation

HRID 2244037 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([C:19]1[CH:44]=[CH:43][C:22]([O:23][CH2:24][C:25]2[CH:26]=[C:27]([NH:31][C:32](=[O:42])[C:33]3[CH:34]=[C:35]([CH:39]=[CH:40][CH:41]=3)[C:36](O)=[O:37])[CH:28]=[CH:29][CH:30]=2)=[C:21]([CH2:45][CH2:46][CH3:47])[C:20]=1[OH:48])(=[O:18])[CH3:17].[CH3:49][C:50]1([CH3:58])[O:55][C:54](=[O:56])[CH2:53][C:52](=[O:57])[O:51]1>ClCCl>[C:16]([C:19]1[CH:44]=[CH:43][C:22]([O:23][CH2:24][C:25]2[CH:26]=[C:27]([NH:31][C:32](=[O:42])[C:33]3[CH:41]=[CH:40][CH:39]=[C:35]([C:36](=[C:53]4[C:54](=[O:56])[O:55][C:50]([CH3:58])([CH3:49])[O:51][C:52]4=[O:57])[OH:37])[CH:34]=3)[CH:28]=[CH:29][CH:30]=2)=[C:21]([CH2:45][CH2:46][CH3:47])[C:20]=1[OH:48])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 11561413N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-isophthalamic acid

Product 1

HCID 54681860N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-3-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-hydroxy-methyl]-benzamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add dicyclohexylcarbodiimide (0.231 g, 1.12 mmol, Aldrich Chemical Co.) to a solution of N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-isophthalamic acid (0.500 g, 1.12 mmol), 2,2-dimethyl-[1,3]dioxane-4,6-dione (0.161 g, 1.12 mmol), and 4-N,N-dimethylaminopyridine (0.273 g, 2.23 mmol, Chem-Impex) in dichloromethane (50 mL, 0.2 M). Filter precipitate, wash filter cake with dichloromethane, and concentrate filtrate. Dilute residue with dichloromethane and wash with 1N hydrochloric acid. Dry the organic layer with sodium sulfate and concentrate to afford the title compound (0.641 g, 1.12 mmol): MS (m/z): 572 (M−1).

Workup

  1. filtrationFilter precipitate
  2. washwash
  3. filtrationfilter cake with dichloromethane
  4. concentrationconcentrate filtrate
  5. washDilute residue with dichloromethane and wash with 1N hydrochloric acid
  6. dry with materialDry the organic layer with sodium sulfate
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-6d547ebc00f24723a57ee01d4ccede19
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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