Triethylamine → HCID 10317969, compound

HRID 2255516Notes

Reaction equation

HRID 2255516 reaction equation
[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.ClC(OCC)=O.[CH2:29]([N:31]1[CH2:35][CH2:34][CH2:33][C@H:32]1[CH2:36][NH2:37])[CH3:30]>O1CCCC1.ClCCl>[CH2:29]([N:31]1[CH2:35][CH2:34][CH2:33][C@H:32]1[CH2:36][NH:37][C:4](=[O:6])[C:3]1[C:7]([O:14][CH3:15])=[C:8]([O:12][CH3:13])[CH:9]=[C:10]([Br:11])[C:2]=1[NH2:1])[CH3:30]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 643457(S)-(-)-2-Aminomethyl-1-ethylpyrrolidineHCID 14668270HCID 14668270, compound

Product 1

HCID 10317969HCID 10317969, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-3-bromo-5,6-dimethoxybenzoic acid (0.96 g, 3 mmol) and triethylamine (0.58 ml, 4.2 mmol) in 15 ml tetrahydrofuran/ /dichloromethane (1:1) was added ethyl chloroformate (0.32 ml, 3.4 mmol) at -20° C. After stirring for 45 min. at -20° C. a solution of (2S)-(-)-1-ethyl-2-aminomethylpyrrolidine in 10 ml dichloromethane was added at -20° C. After stirring for 3 h at room temperature the mixture was washed with water and extracted with 0.5M HCl. The aqueous phase was made alkaline and extracted twice with dichloromethane. Drying (Na2SO4) and evaporation gave 0.45 g crude material which was purified by chromatography on a C18 reversed phase column with H2O/MeOH/NH3 40:60:0.3 as eluent to give 0.25 g (22%) pure product as an oil.

Workup

  1. additionwas added at -20° C
  2. washwas washed with water
  3. extractionextracted with 0.5M HCl
  4. extractionextracted twice with dichloromethane
  5. customDrying
  6. custom(Na2SO4) and evaporation
  7. customgave 0.45 g crude material which
  8. customwas purified by chromatography on a C18 reversed phase column with H2O/MeOH/NH3 40:60:0.3 as eluent

Sources & evidence

ORD record
ord-0631668034cf474c80b80e4a6572272c
Source dataset
uspto-grants-1993_08
Patent number
US05240957

Reaction notes

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