Triethylamine → HCID 90779904, compound

HRID 1986507Notes

Reaction equation

HRID 1986507 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:7]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:6]2[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:45][CH2:46][O:47][C:48]([CH2:50][SH:51])=[O:49].[H-].[Na+]>CN(C)C=O.O1CCCC1>[C:21]([O:20][C:19]([NH:18][CH2:17][C:7]1[C:8]([CH2:13][CH:14]([CH3:16])[CH3:15])=[N:9][C:10]2[C:5]([C:6]=1[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)=[CH:4][C:3]([CH2:2][S:51][CH2:50][C:48]([O:47][CH2:46][CH3:45])=[O:49])=[CH:12][CH:11]=2)=[O:25])([CH3:24])([CH3:23])[CH3:22]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 86605650HCID 86605650, compound

Product 1

HCID 90779904HCID 90779904, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl [6-(hydroxymethyl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methylcarbamate (1.1 g, 2.5 mmol), triethylamine (0.53 ml, 3.8 mmol) and tetrahydrofuran (50 ml) was added methanesulfonyl chloride (0.3 ml, 3.8 mmol) under ice-cooling, and the mixture was stirred for 30 min. A mixture of ethyl thioglycollate (0.42 ml, 3.8 mmol), sodium hydride (60% in oil, 0.15 g, 3.8 mmol) and N,N-dimethylformamide (3 ml) were added to the reaction mixture and the mixture was stirred at room temperature for 15 min. The reaction mixture was partitioned between ethyl acetate and water and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give ethyl ({[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]methyl}thio)acetate (1.1 g, yield 83%) as a white powder.

Workup

  1. temperaturecooling
  2. additionwere added to the reaction mixture
  3. stirringthe mixture was stirred at room temperature for 15 min
  4. customThe reaction mixture was partitioned between ethyl acetate and water
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b4ad071d1470416cae221be5931b17ed
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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