1,2-Dichloroethane → 2-[(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]acetamide

HRID 225967Notes

Reaction equation

HRID 225967 reaction equation
[C:1]1(C2C=CC=CC=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:13][C:12](=[N:14][O:15][CH3:16])[CH2:11][C@H:10]2[CH2:17][C:18]([OH:20])=O)=[O:8])=[CH:3][CH:2]=1.[CH:27]1[CH:28]=[CH:29][C:30]2N(O)N=N[C:31]=2[CH:32]=1.C(Cl)CCl.[NH3:41].O1CCOCC1>O1CCCC1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[C:1]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:2]=[CH:3][C:4]([C:7]([N:9]2[CH2:13][C:12](=[N:14][O:15][CH3:16])[CH2:11][C@H:10]2[CH2:17][C:18]([NH2:41])=[O:20])=[O:8])=[CH:5][CH:6]=1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 312751,4-DioxaneHCID 757711-HydroxybenzotriazoleHCID 131727525[(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl] acetic acid2×

Product 1

HCID 1317275302-[(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]acetamideYield 81%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]acetic acid (intermediate 7, 50 mg, 0.14 mmol) in tetrahydrofuran (4 ml) were added HOBt (29 mg, 0.21 mmol), EDC (41 mg, 0.21 mmol), DMAP (2 mg, 0.01 mmol) followed by ammonia in dioxane (0.425 ml, 2M, 0.21 mmol). The reaction mixture was stirred overnight Ethyl acetate was added and the organic phase was washed with citric acid 5%, NH4Cl, NaHCO3 then brine. The organic phase was dried (MgSO4) and concentrated to afford 2-[(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]acetamide (40 mg). Yield: 81%. HPLC purity: 93%

Workup

  1. additionwas added
  2. washthe organic phase was washed with citric acid 5%, NH4Cl, NaHCO3
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8c9e19a8eb53415e8e37927fd85bca57
Source dataset
uspto-grants-2009_07
Patent number
US07557136B2

Reaction notes

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