tert-Butanol → HCID 70222659, compound

HRID 1033991Notes

Reaction equation

HRID 1033991 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([OH:20])([CH3:19])([CH3:18])[CH3:17].[CH2:21]([O:23][C:24]1[CH:32]=[C:31]([CH2:33][C:34]([NH:36][CH:37]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[N:47]2[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]2)[CH2:38][CH2:39][CH3:40])=[O:35])[CH:30]=[CH:29][C:25]=1[C:26](O)=[O:27])[CH3:22]>C(Cl)Cl.[Cu]Cl>[CH2:21]([O:23][C:24]1[CH:32]=[C:31]([CH2:33][C:34]([NH:36][CH:37]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[N:47]2[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]2)[CH2:38][CH2:39][CH3:40])=[O:35])[CH:30]=[CH:29][C:25]=1[C:26]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:27])[CH3:22]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 10694323HCID 10694323, compound

Product 1

HCID 70222659HCID 70222659, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1.9 g (9.6 mmols) of N,N'-dicyclohexyl-carbodiimide, 1.06 ml (11.2 mmols) of absolute tert.butanol and 0.020 g (0.20 mmol) of copper(I) chloride was stirred for 60 hours at room temperature. Then, 6.6 ml of methylene chloride were added, and the resulting solution was added dropwise to a solution of 0.44 g (1 mmol) of 2-ethoxy-4-[N-{1-(2-piperidino-phenyl)-1-butyl}-aminocarbonylmethyl]-benzoic acid in 15 ml of methylene chloride. After 60 hours' stirring at 20° C., the precipitate which had formed was filtered off, washed with methylene chloride, and the methylene chloride solution was evaporated in vacuo. The evaporation residue was purified by column chromatography on silica gel (chloroform/ethyl acetate-9/1).

Workup

  1. stirringAfter 60 hours' stirring at 20° C.
  2. customthe precipitate which had formed
  3. filtrationwas filtered off
  4. washwashed with methylene chloride
  5. customthe methylene chloride solution was evaporated in vacuo
  6. customThe evaporation residue was purified by column chromatography on silica gel (chloroform/ethyl acetate-9/1)

Sources & evidence

ORD record
ord-51e972fd1d3e4aaabf6d5ba7450a14f9
Source dataset
uspto-grants-1994_05
Patent number
US05312924

Reaction notes

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