Acetyl chloride → HCID 57741541, compound

HRID 416012Notes

Reaction equation

HRID 416012 reaction equation
[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([N:28]5[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]5)=[O:27])=[CH:22][CH:21]=4)=[CH:15][C:14]=3[Cl:34])[C:8]2=[O:35])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[C:38](Cl)(=[O:40])[CH3:39]>ClCCl>[C:38]([N:31]1[CH2:30][CH2:29][N:28]([C:26]([C:23]2[CH:22]=[CH:21][C:20]([C:16]3[CH:15]=[C:14]([Cl:34])[C:13]([CH2:12][CH:9]4[CH2:10][CH2:11][N:7]([CH:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)[C:8]4=[O:35])=[C:18]([Cl:19])[CH:17]=3)=[CH:25][CH:24]=2)=[O:27])[CH2:33][CH2:32]1)(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 57741513HCID 57741513, compound

Product 1

HCID 57741541HCID 57741541, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve racemic 1-cyclohexyl-3-[3,5-dichloro-4′-(piperazine-1-carbonyl)-biphenyl-4-ylmethyl]-pyrrolidin-2-one (0.082 g, 0.158 mmol) in dichloromethane (5 mL), add 1.0 N sodium hydroxide solution (0.5 mL) and acetyl chloride (0.020 mL, 0.281 mmol). Stir the mixture, sealed, overnight at room temperature. Dilute reaction with dichloromethane (20 mL) and wash with 1.0 N sodium hydroxide (10 mL) then brine (5 mL). Collect the organic phase, dry over anhydrous magnesium sulfate and concentrate under reduced pressure. Purify via flash chromatography by eluding with a gradient (100%) dichloromethane to 5% ammonia methanol/95% dichloromethane to obtain 0.065 g (74%) of product as a white foam: MS (m/z): 556 (M+).

Workup

  1. customsealed, overnight at room temperature
  2. additionDilute
  3. washwash with 1.0 N sodium hydroxide (10 mL)
  4. customCollect the organic phase
  5. dry with materialdry over anhydrous magnesium sulfate
  6. concentrationconcentrate under reduced pressure
  7. customPurify via flash chromatography

Sources & evidence

ORD record
ord-335fdeb91fc144cf814ec3d33920d88d
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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