1,2-Dichloroethane → 1-(3-fluoro-4-methoxyphenyl)-N-methoxy-N-methyl-5-oxopyrrolidine-3-carboxamide

HRID 1993384Notes

Reaction equation

HRID 1993384 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]([OH:18])=O)[CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl.[CH3:20][O:21][NH:22][CH3:23].C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]([N:22]([O:21][CH3:20])[CH3:23])=[O:18])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 433803921-(3-Fluoro-4-methoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 866089631-(3-fluoro-4-methoxyphenyl)-N-methoxy-N-methyl-5-oxopyrrolidine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(3-fluoro-4-methoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid (5 g, 19.7 mmol), N-methoxymethanamine hydrochloride (2.18 g, 22.4 mmol), HOBt (4.0 g, 29.7 mmol) and Et3N (4.2 mL, 29.7 mmol) in 60 mL of DMF was added EDC (5.7 g, 29.7 mmol) at 0° C. The reaction was warmed to RT in 1 h and stirred at RT for 16 h. The mixture was diluted with 100 mL of EtOAc, and the resulted solution was washed with 50 mL of satd. NaHCO3 followed by 50 mL of brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude residue was re-crystallized in 80% EtOAc/hexane to afford white solid. MS (ESI pos. ion) m/z: 297.3 (M+H). Calc'd Exact Mass for C14H17FN2O4: 296.29.

Workup

  1. washthe resulted solution was washed with 50 mL of satd
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was re-crystallized in 80% EtOAc/hexane
  5. customto afford white solid

Sources & evidence

ORD record
ord-571c5a33b495404092f20bf9bd0addb7
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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