Triethylamine → HCID 69203944, compound

HRID 1393839Notes

Reaction equation

HRID 1393839 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1C.[CH3:12][O:13][C:14](=[O:21])[C@H:15]([CH2:17][CH2:18][S:19][CH3:20])[NH2:16].C(N(CC)CC)C>CN1CCCC1=O>[CH3:12][O:13][C:14](=[O:21])[CH:15]([NH:16][C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1)[CH2:17][CH2:18][S:19][CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64684methyl (2S)-2-amino-4-(methylsulfanyl)butanoateHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

Product 1

HCID 69203944HCID 69203944, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

1 g of 4-fluoro-3-methylnitrobenzene, 0.694 g of L-methionine methyl ester and 1.09 ml of triethylamine were added to a solution of 5 ml of N-methylpyrrolidinone. The reaction medium was heated at 90° C. for 7 hours and, after cooling to room temperature, was poured into an ice water mixture. The reaction medium was then extracted with ethyl acetate and the organic phase was dried and concentrated to dryness. After purification by chromatography on a column of silica, 4-methylsulfanyl-2-(4-nitrophenylamino)butyric acid methyl ester (28) was obtained.

Workup

  1. temperatureafter cooling to room temperature
  2. extractionThe reaction medium was then extracted with ethyl acetate
  3. customthe organic phase was dried
  4. concentrationconcentrated to dryness
  5. customAfter purification by chromatography on a column of silica

Sources & evidence

ORD record
ord-0d42beb8f57f420b8e9128a26cbbe037
Source dataset
uspto-grants-2008_03
Patent number
US07347879B2

Reaction notes

Loading…