Trifluoroacetic acid → HCID 66584007, compound

HRID 1972628Notes

Reaction equation

HRID 1972628 reaction equation
O=[C:2]([C:23]#[C:24][CH3:25])[CH2:3][N:4]([S:15]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)(=[O:17])=[O:16])[CH2:5][CH2:6][NH:7]C(=O)OC(C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:23]([CH:2]1[NH:7][CH2:6][CH2:5][N:4]([S:15]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)(=[O:17])=[O:16])[CH2:3]1)#[C:24][CH3:25]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 66583503Tert-butyl (2-((2-oxo-3-pentyn-1-yl)(2-thiophenylsulfonyl)amino)ethyl)carbamate

Product 1

HCID 66584007HCID 66584007, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2-((2-oxo-3-pentyn-1-yl)(2-thiophenylsulfonyl)amino)ethyl)carbamate (330 mg, 0.854 mmol) in CH2Cl2 (10 mL) was added sodium triacetoxyborohydride (1.0 g, 4.72 mmol, Sigma-Aldrich, St. Louis, Mo.) followed by TFA (2.5 mL, 32.4 mmol). The mixture was stirred at room temperature for 1 h and then concentrated to half the original volume. MeOH (5 mL) was added and the solution was concentrated by one-third and then partitioned between NaOH (0.5 N, 20 mL) and CHCl3 (containing 10% i-PrOH) (20 mL). The aqueous layer was extracted twice with CHCl3 (containing 10% i-PrOH) and the combined organic extracts were dried over Na2SO4, filtered, and concentrated to orange oil. The residue was purified by chromatography on silica gel using (1 to 5% MeOH in EtOAc) to give 3-(1-propyn-1-yl)-1-(2-thiophenylsulfonyl)piperazine as a light-yellow film (150 mg).

Workup

  1. concentrationconcentrated to half the original volume
  2. additionMeOH (5 mL) was added
  3. concentrationthe solution was concentrated by one-third
  4. custompartitioned between NaOH (0.5 N, 20 mL) and CHCl3 (containing 10% i-PrOH) (20 mL)
  5. extractionThe aqueous layer was extracted twice with CHCl3 (containing 10% i-PrOH)
  6. dry with materialthe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to orange oil
  9. customThe residue was purified by chromatography on silica gel using (1 to 5% MeOH in EtOAc)

Sources & evidence

ORD record
ord-cb3cf781053844978a14e8201844280b
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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