Furan → HCID 23441033, compound

HRID 2119352Notes

Reaction equation

HRID 2119352 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[Li].[O:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1.C([Li])CCC.[CH3:17][S:18]([C:21]1[CH:40]=[CH:39][C:24]([CH2:25][N:26]2[CH2:32][CH2:31][CH2:30][N:29]([CH2:33][CH2:34][C:35](OC)=[O:36])[CH2:28][CH2:27]2)=[CH:23][CH:22]=1)(=[O:20])=[O:19].[Cl-].[NH4+]>C1COCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:35]([C:8]1[O:7][CH:11]=[CH:10][CH:9]=1)([OH:36])[CH2:34][CH2:33][N:29]1[CH2:30][CH2:31][CH2:32][N:26]([CH2:25][C:24]2[CH:39]=[CH:40][C:21]([S:18]([CH3:17])(=[O:20])=[O:19])=[CH:22][CH:23]=2)[CH2:27][CH2:28]1

Participants

7

Reactant 5

HCID 8029FuranHCID 25517Ammonium ChlorideHCID 23441055HCID 23441055, compoundHCID 178418296HCID 178418296, compoundHCID 178418339Butyllithium

Product 1

HCID 23441033HCID 23441033, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-furyl lithium prepared in 50 mL of THF using 3 mL of furan and 2 mL of 1.63 M n-butyllithium was added dropwise at 0° C., a 10 ml solution in THF of 99 mg of methyl 3-[4-{4-(methylsulfonyl)benzyl}homopiperazinyl]propionate. After stirring at 0° C. for 1 hour, the mixture was mixed with 50 mL of an aqueous saturated ammonium chloride, and extracted with 50 mL×2 of ethyl acetate. The extracts were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography (silica gel, ethyl acetate) to give 62 mg of the titled compound.

Workup

  1. additionwas added dropwise at 0° C.
  2. extractionextracted with 50 mL×2 of ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-77afb28c55b340abaa97c2fa4a976e62
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

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