Ethyl Acetate → HCID 178487875, compound

HRID 1422973Notes

Reaction equation

HRID 1422973 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH:15]=[O:16])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl:18][C:19]1[CH:20]=[N:21][C:22]2[C:27]([C:28]=1[CH:29]=[O:30])=[N:26][C:25]([O:31][CH3:32])=[CH:24][CH:23]=2.N1CCC[C@H]1C(O)=O.C(OCC)(=O)C>CS(C)=O.O>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([CH:14]([CH:15]=[O:16])[CH:29]([C:28]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([O:31][CH3:32])[N:26]=3)[N:21]=[CH:20][C:19]=2[Cl:18])[OH:30])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 145742L-ProlineHCID 866715503-Chloro-6-methoxy-[1,5]naphthyridine-4-carbaldehydeHCID 178453924HCID 178453924, compound

Product 1

HCID 178487875HCID 178487875, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of [trans-4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (3.1 g, 25.1 mmol, 1.0 eq), 3-chloro-6-methoxy-[1,5]naphthyridine-4-carbaldehyde (5.6 g, 25.1 mmol, 1.0 eq) and L-proline (1.16 mg, 10.1 mmol, 0.4 eq) in dimethyl sulfoxide (100 mL) and water (15 mL) is stirred at room temperature for 16 hours. The reaction mixture is then extracted with ethyl acetate (500 mL) and water (500 mL). The organic layer is washed with brine (300 mL), dried over magnesium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: ethyl acetate:petroleum ether, 1:1, v/v) to afford {trans-4-[2-(3-chloro-6-methoxy-[1,5]naphthyridin-4-yl)-1-formyl-2-hydroxy-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester as a light yellow solid (4.5 g, 39% yield).

Workup

  1. extractionThe reaction mixture is then extracted with ethyl acetate (500 mL) and water (500 mL)
  2. washThe organic layer is washed with brine (300 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue that
  7. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-bd7928ae951b4003b0adba04bb4ecab1
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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