Pivaloyl chloride → 5-Chloro-N-(2,2-dimethyl-propionyl)-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzenesulfonamide

HRID 11665Notes

Reaction equation

HRID 11665 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]([N:16]2[CH2:21][C@H:20]([CH3:22])[N:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:18][C@H:17]2[CH3:31])=[O:15])=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:7]=1.[CH3:32][C:33]([CH3:38])([CH3:37])[C:34](Cl)=[O:35]>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]([N:16]2[CH2:21][C@H:20]([CH3:22])[N:19]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)[CH2:18][C@H:17]2[CH3:31])=[O:15])=[C:6]([S:8]([NH:11][C:34](=[O:35])[C:33]([CH3:38])([CH3:37])[CH3:32])(=[O:9])=[O:10])[CH:7]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 692957585-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzenesulfonamide

Product 1

HCID 696555115-Chloro-N-(2,2-dimethyl-propionyl)-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzenesulfonamideYield 49.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzenesulfonamide (0.050 g, 0.11 mmol) in acetonitrile (1.0 mL) was added 2,2-dimethyl-propionyl chloride (0.050 g, 0.47 mmol) and 1,8-diazobicyclo[5.4.0]undec-7-ene (0.25 mL, 1.64 mmol). The resulting reaction mixture was heated to 50° C. for 2 hours, concentrated in vacuo and purified by silica gel chromatography to give the title compound (0.030 g, LRMS: 554.4).

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-257dad64d63a46bebcfd286475670895
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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