Methanesulfonyl chloride → (S)-4-(tert-butoxycarbonyl)-1-(3-chlorophenyl)-5-[2-(methanesulfonyloxy)ethyl]piperazin-2-one

HRID 342138Notes

Reaction equation

HRID 342138 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][CH2:15][OH:16])[CH2:12][N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[C:10](=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][CH2:15][O:16][S:35]([CH3:34])(=[O:37])=[O:36])[CH2:12][N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[C:10](=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 20691434(S)-4-(tert-butoxycarbonyl)-1-(3-chlorophenyl)-5-(2-hydroxyethyl)piperazin-2-one

Product 1

HCID 22941056(S)-4-(tert-butoxycarbonyl)-1-(3-chlorophenyl)-5-[2-(methanesulfonyloxy)ethyl]piperazin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the alcohol from Step E (3.58 g, 10.1 mmol) in 50 mL of dichloromethane at 0° C. was added diisopropylethylamine (3.5 mL, 20.2 mmol), followed by methanesulfonyl chloride (0.936 mL, 12.1 mmol). The solution was stirred for 45 minutes, then quenched with 10% citlic acid. The solution was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product which was used in the next step without further purification.

Workup

  1. customquenched with 10% citlic acid
  2. washThe solution was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff637fca470a4c64a31f0cbff285afac
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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