Tert-butyl 2-oxo-4-(2-thiophenylsulfonyl)-1-piperazinecarboxylate → Tert-butyl (2-((2-oxo-3-pentyn-1-yl)(2-thiophenylsulfonyl)amino)ethyl)carbamate

HRID 1972627Notes

Reaction equation

HRID 1972627 reaction equation
[O:1]=[C:2]1[CH2:7][N:6]([S:8]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)(=[O:10])=[O:9])[CH2:5][CH2:4][N:3]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[C:23]([Mg]Br)#[C:24][CH3:25]>C1COCC1>[O:1]=[C:2]([C:23]#[C:24][CH3:25])[CH2:7][N:6]([S:8]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)(=[O:10])=[O:9])[CH2:5][CH2:4][NH:3][C:16](=[O:17])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 66582797Tert-butyl 2-oxo-4-(2-thiophenylsulfonyl)-1-piperazinecarboxylateHCID 178419101HCID 178419101, compound2×

Product 1

HCID 66583503Tert-butyl (2-((2-oxo-3-pentyn-1-yl)(2-thiophenylsulfonyl)amino)ethyl)carbamateYield 80.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 2-oxo-4-(2-thiophenylsulfonyl)-1-piperazinecarboxylate (600 mg, 1.73 mmol) in THF (8 mL) at 0° C. was added to a solution of 1-propynylmagnesium bromide (0.5 M in THF, 5.0 mL, 2.50 mmol, Sigma-Aldrich, St. Louis, Mo.). After 1.5 h at 0° C., additional 1-propynylmagnesium bromide (3.0 mL, 1.50 mmol) was added. After an additional 50 min, the mixture was quenched with ice (20 g) and saturated aqueous NH4Cl (15 mL). EtOAc (20 mL) was added and the aqueous layer was further extracted with EtOAc (2×10 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel using (10 to 50% EtOAc in hexane) to give tert-butyl (2-((2-oxo-3-pentyn-1-yl)(2-thiophenylsulfonyl)amino)ethyl)carbamate as yellow oil (540 mg).

Workup

  1. waitAfter an additional 50 min
  2. customthe mixture was quenched with ice (20 g) and saturated aqueous NH4Cl (15 mL)
  3. additionEtOAc (20 mL) was added
  4. extractionthe aqueous layer was further extracted with EtOAc (2×10 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel using (10 to 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-06ea812859de45d38ffb6542d1ac6661
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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