Nitrogen → HCID 66764668, compound

HRID 1466815Notes

Reaction equation

HRID 1466815 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([S:13]CCC(OCCCCCCCC)=O)[CH:6]=1)[CH3:2].N#N.CC(C)([O-])C.[K+]>C1COCC1>[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([SH:13])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 947NitrogenHCID 23665647Potassium tert-butoxideHCID 66765112HCID 66765112, compound

Product 1

HCID 66764668HCID 66764668, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-Methoxy-3-(2-octyloxycarbonyl-ethylsulfanyl)-benzoic acid ethyl ester (2.93 g, 7.40 mmol) was dissolved in THF and the mixture was chilled to −78° C. N2 (g) was bubbled through the reaction mixture and potassium tert-butoxide (8.88 mL, 1.0M in THF, 8.88 mmol) was added via syringe over 2 minutes. The reaction was stirred at −78° C. for 1 hour then slowly allowed to warm to 10° C. for 2 hours. The reaction was then quenched with 1N aq. HCl (30 mL) and submitted to standard aqueous workup. The residue was purified by silica gel chromatography (0-10% EtOAc in hexanes:MeOH (98:2)) to afford the title compound.

Workup

  1. additionwas added via syringe over 2 minutes
  2. temperatureto warm to 10° C. for 2 hours
  3. customThe reaction was then quenched with 1N aq. HCl (30 mL)
  4. customThe residue was purified by silica gel chromatography (0-10% EtOAc in hexanes:MeOH (98:2))

Sources & evidence

ORD record
ord-5836bb60141345fe8711055cef0d6512
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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