Carbon Dioxide → HCID 23120833, compound

HRID 1454813Notes

Reaction equation

HRID 1454813 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].[C:32](=[O:34])=[O:33]>C1COCC1.C1COCC1.CCCCCCC.C(C1C=CC=CC=1)C>[C:15]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:17][C:12]([S:9]([NH:8][C:6]2[N:7]=[C:2]([CH2:1][C:32]([OH:34])=[O:33])[CH:3]=[CH:4][CH:5]=2)(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 2724682Lithium diisopropylamideHCID 4982676HCID 4982676, compound

Product 1

HCID 23120833HCID 23120833, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22742125Tetrahydrofuran heptane ethylbenzolSolvent

Conditions

Temperature
-20 °C

Procedure

Biphenyl-4-sulfonic acid (6-methyl-pyridin-2-yl)-amide (0.5 g, product of example 5) under an argon atmosphere in THF (5 mL) was cooled to −20° C. and treated dropwise at −20° C. with 1.54 mL of a 2 M solution of lithium diisopropylamide in THF/heptane/ethylbenzene (Fluka). The solution was stirred 1 h at −20° C., cooled to −70° C. and then treated with an access of dry ice. The mixture was allowed to warm to RT (1 h), partitioned between diluted aqueous HCl and AcOEt. The layers were separated, the aqueous layer extracted twice with AcOEt, the combined organic layers dried over Na2SO4, filtered and evaporated to give [6-(biphenyl-4-sulfonylamino)-pyridin-2-yl]-acetic acid as light yellow gum (0.779 g) that was used without further purification in the next step.

Workup

  1. temperaturecooled to −70° C.
  2. temperatureto warm to RT (1 h)
  3. custompartitioned between diluted aqueous HCl and AcOEt
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted twice with AcOEt
  6. dry with materialthe combined organic layers dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-25fdac697bea4ca9bd93c8964ad061cb
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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