Carbon Dioxide → HCID 136005769, compound

HRID 915938Notes

Reaction equation

HRID 915938 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15](=[O:29])[C:16]3[C:21]([CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[N:20][N:19]([CH3:28])[C:17]=3[N:18]=2)=[C:9]([O:30][CH3:31])[CH:8]=1.[C:32](=[O:34])=[O:33].[OH-].[Na+]>O1CCCC1>[CH:22]1([C:21]2[C:16]3[C:15](=[O:29])[NH:14][C:13]([C:10]4[CH:11]=[CH:12][C:7]([C:32]([OH:34])=[O:33])=[CH:8][C:9]=4[O:30][CH3:31])=[N:18][C:17]=3[N:19]([CH3:28])[N:20]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 136005920HCID 136005920, compoundHCID 178418339Butyllithium

Product 1

HCID 136005769HCID 136005769, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen, 1.6 ml of n-butyl lithium (1.56M hexane solution 2.5 mmol) was added dropwise at −78° C. to a 10 ml tetrahydrofuran solution of 500 mg (1.20 mmol) of the compound obtained in Example 26. The mixture was stirred at the same temperature for 30 minutes, and then a carbon dioxide gas was blown into the reaction mixture for 45 minutes. Further, the reaction mixture was stirred at −78° C. for 2 hours, and then brought to room temperature. The reaction mixture was alkalinized by addition of a 1M aqueous solution of sodium hydroxide, and washed with dichloromethane. The aqueous layer was acidified with a 6M aqueous solution of hydrochloric acid, and precipitated solids were collected by filtration, obtaining 200 mg (44%) of the captioned compound.

Workup

  1. stirringFurther, the reaction mixture was stirred at −78° C. for 2 hours
  2. custombrought to room temperature
  3. washwashed with dichloromethane
  4. customprecipitated solids
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-febb131016f84a3697febb8839eae866
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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