Ethyl Acetate → HCID 68511840, compound

HRID 1947104Notes

Reaction equation

HRID 1947104 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH:9]1[CH:13]([O:14][Si](C(C)(C)C)(C)C)[CH2:12][N:11]([C:22](=[O:30])[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:10]1)[C:5](=[O:8])[CH2:6]Cl.NCCN(C1C(O)CN(C(=O)C2C=CC(Cl)=CC=2)C1)C(=O)CCl.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:22]([N:11]2[CH2:12][CH:13]([OH:14])[CH:9]([N:4]3[CH2:3][CH2:2][NH:1][CH2:6][C:5]3=[O:8])[CH2:10]2)=[O:30])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 68511389HCID 68511389, compoundHCID 68513829HCID 68513829, compound

Product 1

HCID 68511840HCID 68511840, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N-(2-amino-ethyl)-N-[4-(tert-butyl-dimethyl-silanyloxy)-1-(4-chloro-benzoyl)-pyrrolidin-3-yl]-2-chloro-acetamide and N-(2-amino-ethyl)-2-chloro-N-[1-(4-chloro-benzoyl)-4-hydroxy-pyrrolidin-3-yl]-acetamide (200 mg) was dissolved in 2 mL of DMF. Then K2CO3 (117 mg, 0.84 mmol) and Cat. KI were added. The mixture was stirred at 90° C. for overnight. EtOAc (5 mL) was added. The organic phase was washed with Sat. NaHCO3, dried over Na2SO4, and concentrated. The residue was purified by column chromatography (Ethyl acetate:Methanol:Et3N:3:1:0.04) to give the desired product (50 mg, 37% yield) as a colorless oil. MS (ESI), M/Z, 324 (M+1). Retention time: 1.13 min (FA-polar).

Workup

  1. additionKI were added
  2. washThe organic phase was washed with Sat. NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (Ethyl acetate:Methanol:Et3N:3:1:0.04)

Sources & evidence

ORD record
ord-d9a87a7b1cf141fb83e561605620ecf9
Source dataset
uspto-grants-2013_03
Patent number
US08399455B2

Reaction notes

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