tert-Butanol → HCID 14423206, compound

HRID 1193744Notes

Reaction equation

HRID 1193744 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:9][C:10]1[C:15]([C:16]([C:18]2[CH2:22][CH2:21][CH2:20][C:19]=2N2CCCC2)=[O:17])=[CH:14][CH:13]=[CH:12][N:11]=1.C(O)(C)(C)C>C(N(CC)CC)C>[Cl:9][C:10]1[C:15]([C:16]([C:18]2[CH2:22][CH2:21][CH2:20][C:19]=2[NH:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:17])=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 2723640Glycine ethyl ester, hydrochlorideHCID 11011278HCID 11011278, compound

Product 1

HCID 14423206HCID 14423206, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Add equimolar amounts of ethyl glycinate hydrochloride, triethylamine, and (2-chloro-3-pyridinyl)-[2-(1-pyrrolidinyl)-1-cyclopenten-1-yl]methanone to t-butyl alcohol (170 ml per 0.020 mole of amine). Reflux the resulting mixture for 34 hrs, monitoring the reaction by thin-layer chromatography as needed. Cool the reaction mixture, and evaporate solvent. Wash a CHCl3 solution of the residue with water and with saturated aqueous NaCl solution. After drying the organic solution, evaporate the solvent to obtain the resulting enaminoketone, (2-chloro-3-pyridinyl)[2-(1-ethoxycarbonylmethanaminyl)-1-cyclopenten-1-yl]methanone, m.p. 114.5°-117.5° C., after recrystallization from isopropanol.

Workup

  1. temperatureReflux the resulting mixture for 34 hrs
  2. customthe reaction by thin-layer chromatography
  3. temperatureCool the reaction mixture
  4. customevaporate solvent
  5. washWash a CHCl3 solution of the residue with water
  6. customAfter drying the organic solution
  7. customevaporate the solvent

Sources & evidence

ORD record
ord-9f6650d8112c481e82c279c20a870eeb
Source dataset
uspto-grants-1989_03
Patent number
US04810708

Reaction notes

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