Dimethyl Sulfoxide → (S)-4-(tert-butoxycarbonyl)-1-(3-chlorophenyl)-5-[2-(oxo)ethyl]piperazin-2-one

HRID 342141Notes

Reaction equation

HRID 342141 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[C@@H:23]([CH2:24][CH2:25][OH:26])[CH2:22][N:21]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[C:20](=[O:34])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16]([N:18]1[C@@H:23]([CH2:24][CH:25]=[O:26])[CH2:22][N:21]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[C:20](=[O:34])[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 20691434(S)-4-(tert-butoxycarbonyl)-1-(3-chlorophenyl)-5-(2-hydroxyethyl)piperazin-2-one

Product 1

HCID 88302437(S)-4-(tert-butoxycarbonyl)-1-(3-chlorophenyl)-5-[2-(oxo)ethyl]piperazin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of oxalyl chloride (0.608 mL, 6.97 mmol) in dichloromethane (40 mL) at -78° C. was added DMSO (0.990 mL, 13.9 mmol) over 2-3 minutes. The solution was stirred for 10 minutes, then a solution of the alcohol from Step E of Example 43 (2.06 g, 5.81 mmol) in 10 mL of dichloromethane was added over 5 minutes, keeping the reaction temperature below -70° C. The reaction was stirred for 10 minutes, then triethylamine (2.43 mL) was added, and the reaction was stirred at -78° C. for 5 minutes, then allowed to warm to room temperature. After 45 minutes, the solution was poured into dichloromethane, and washed with sat. NH4Cl soln., 10% citric acid soln., water, and brine. The solution was dried (Na2SO4), filtered, and concentrated in vacuo to provide the titled aldehyde.

Workup

  1. customthe reaction temperature below -70° C
  2. stirringThe reaction was stirred for 10 minutes
  3. stirringthe reaction was stirred at -78° C. for 5 minutes
  4. waitAfter 45 minutes
  5. washwashed with sat. NH4Cl soln
  6. dry with materialThe solution was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a353eda57ff4f19a2103513c2baf0e3
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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