Carbon Dioxide → HCID 22165626, compound

HRID 1906774Notes

Reaction equation

HRID 1906774 reaction equation
C([Li])CCC.[Cl:6][C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[CH:14]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:24])[NH:17][C:16]([CH2:25][O:26][CH2:27][C:28]#[CH:29])=[C:15]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].[C:35](=[O:37])=[O:36]>CCCCCC.O1CCCC1>[Cl:6][C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[CH:14]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:24])[NH:17][C:16]([CH2:25][O:26][CH2:27][C:28]#[C:29][C:35]([OH:37])=[O:36])=[C:15]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

6

Reactant 3

HCID 280Carbon Dioxide2×HCID 14547436HCID 14547436, compoundHCID 178418339Butyllithium

Product 1

HCID 22165626HCID 22165626, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A 1.6M solution of n-butyllithium in hexane (45 ml) was added dropwise to a solution of 1-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-2-propyne (132 g) in tetrahydrofuran (1 l.) keeping the temperature below -40°. The mixture was stirred at -60° for 2 hours and then carbon dioxide gas was passed through the solution for 30 minutes with cooling in an acetone/solid carbon dioxide bath. The mixture was allowed to warm to 0° while the passage of carbon dioxide gas was continued and then it was quenched with water (1 l.) and the layers separated. The aqueous layer was extracted into ether (500 ml) and the combined organic layers were washed with water, diluted with dichloromethane, washed with 1M HCl, dried over MgSO4 and evaporated. The residue was triturated with methanol and the resulting solid collected, washed with cold (-20°) methanol and dried to give 4-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}but-2-ynoic acid, (83.7 g), m.p. 150°-152°.

Workup

  1. customthe temperature below -40°
  2. temperaturewith cooling in an acetone/solid carbon dioxide bath
  3. customit was quenched with water (1 l.)
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted into ether (500 ml)
  6. washthe combined organic layers were washed with water
  7. additiondiluted with dichloromethane
  8. washwashed with 1M HCl
  9. dry with materialdried over MgSO4
  10. customevaporated
  11. customThe residue was triturated with methanol
  12. customthe resulting solid collected
  13. washwashed with cold (-20°) methanol
  14. customdried

Sources & evidence

ORD record
ord-0eea5199cddb4a728a69b68efc1730db
Source dataset
uspto-grants-1987_03
Patent number
US04654353

Reaction notes

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