4-Chlorobenzoyl chloride → HCID 68509333, compound

HRID 1947105Notes

Reaction equation

HRID 1947105 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]2[CH2:12][CH:11]([OH:13])[CH:10]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][C:15]3=[O:20])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1>C(Cl)Cl>[Cl:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([N:17]2[CH2:18][CH2:19][N:14]([CH:10]3[CH:11]([OH:13])[CH2:12][N:8]([C:6](=[O:7])[C:5]4[CH:21]=[CH:22][C:2]([Cl:1])=[CH:3][CH:4]=4)[CH2:9]3)[C:15](=[O:20])[CH2:16]2)=[O:38])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 68511840HCID 68511840, compound

Product 1

HCID 68509333HCID 68509333, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[1-(4-Chloro-benzoyl)-4-hydroxy-pyrrolidin-3-yl]-piperazin-2-one (50 mg, 0.15 mmol) in CH2Cl2 (1 mL) at 0° C., was added DIPEA (27 uL, 0.154 mmol) and 4-Chloro-benzoyl chloride (20 uL, 0.154 mmol). The mixture was stirred at RT for 4 h. The organic phase was washed with Sat. NaHCO3, dried over Na2SO4, and concentrated. The residue was purified by column chromatography (Ethyl acetate:Methanol:Et3N:10.1:0.1) to give the desired product (36 mg, 50% yield) as a white solid. MS: (ESI), M/Z, 462 (M+1). Retention time: 2.25 min (FA-polar).

Workup

  1. washThe organic phase was washed with Sat. NaHCO3
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (Ethyl acetate:Methanol:Et3N:10.1:0.1)

Sources & evidence

ORD record
ord-a1da1f171f544f158d67b9bf8701e558
Source dataset
uspto-grants-2013_03
Patent number
US08399455B2

Reaction notes

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