Ethyl bromoacetate → (S)-N-(alpha-ethylbenzyl)-3-(ethoxycarbonylmethoxy)-2-phenylquinoline-4-carboxamide

HRID 651058

Reaction equation

HRID 651058 reaction equation
[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]=1[OH:29])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]>C1COCC1>[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:14]=1[O:29][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 5311424Talnetant

Product 1

HCID 10790452(S)-N-(alpha-ethylbenzyl)-3-(ethoxycarbonylmethoxy)-2-phenylquinoline-4-carboxamideYield 135.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g (5.2 mmol) of (S)-N-(α-ethylbenzyl)-3-hydroxy-2-phenylquinoline-4-carboxamide (compound of Description 1) were dissolved, under nitrogen atmosphere and magnetic stirring, in 20 ml of THF. 2.0 g (14.5 mmol) of K2CO3, 0.87 ml (7.8 mmol) of ethyl bromoacetate and a small amount of Ki were added and the reaction mixture was left at room temperature under magnetical stirring for 2.5 hours. The precipitate was filtered off and the solution was evaporated in-vacuo to dryness; the residue was dissolved in water and extracted with EtOAc; the organic phase was separated, dried over Na2SO4 and evaporated in-vacuo to dryness to obtain 3.3 g of a dense yellow oil. The oil was purified by flash chromatography on 230-400 mesh silica gel, eluting with a mixture of hexane/EtOAc 70:30 containing 0.5% of 28% NH4OH, and the purified product was triturated with i-Pr2O/i-PrOH to yield 2.1 g of the title compound as a white solid.

Workup

  1. waitthe reaction mixture was left at room temperature
  2. filtrationThe precipitate was filtered off
  3. customthe solution was evaporated in-vacuo to dryness
  4. dissolutionthe residue was dissolved in water
  5. extractionextracted with EtOAc
  6. customthe organic phase was separated
  7. dry with materialdried over Na2SO4
  8. customevaporated in-vacuo to dryness

Sources & evidence

ORD record
ord-2a3a07e9fb27485ca89468948fa5f9ad
Source dataset
uspto-grants-2001_08
Patent number
US06277862B1

Linked notes

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