Chloroacetyl chloride → 4-tert-Butoxycarbonyl-5(S)-n-butyl-1-(2-methylphenyl)piperazin-2-one

HRID 342157Notes

Reaction equation

HRID 342157 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][C@@H:10]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:12][CH2:13][CH3:14].Cl[CH2:24][C:25](Cl)=[O:26]>C(OCC)(=O)C>[C:19]([O:18][C:16]([N:15]1[C@@H:10]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:9][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[C:25](=[O:26])[CH2:24]1)=[O:17])([CH3:21])([CH3:20])[CH3:22]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 22941063HCID 22941063, compound

Product 1

HCID 153910114-tert-Butoxycarbonyl-5(S)-n-butyl-1-(2-methylphenyl)piperazin-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared essentially according to the procedure described in Example 39. Step D, except using N-(2-methylphenyl)-2(S)-(tert-butoxycarbonylamino)hexanamine (0.506 g, 1.65 mmol), chloroacetyl chloride (0.158 mL, 1.98 mmol) in ethyl acetate-saturated sodium bicarbonate at 0° C. The crude product thus obtained was dissolved in DMF (15 mL), cooled to 0° C. under nitrogen, and treated with cesium carbonate (1.61 g, 4.95 mmol). The reaction was stirred at 0° C. for 2 h, and at room temperature for 2 h. The reaction was quenched with saturated ammonium chloride, and extracted with ethyl acetate. The extracts were dried and evaporated to give the title compound.

Workup

  1. customat 0° C
  2. customThe crude product thus obtained

Sources & evidence

ORD record
ord-3c6bb7e18d774f869d5d54163b47d153
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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