Triethylamine → HCID 59497651, compound

HRID 1747408Notes

Reaction equation

HRID 1747408 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].Cl.[C:12]([O:16][C:17](=[O:22])[C:18]([NH2:21])([CH3:20])[CH3:19])([CH3:15])([CH3:14])[CH3:13].CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[C:12]([O:16][C:17](=[O:22])[C:18]([CH3:20])([NH:21][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])[CH3:19])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 738951-Fluoro-2-nitrobenzeneHCID 12186776Tert-butyl 2-amino-2-methylpropanoate hydrochloride

Product 1

HCID 59497651HCID 59497651, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 1-fluoro-2-nitrobenzene (485 μL, 4.6 mmol) and 2-amino-2-methyl-propionic acid tert-butyl ester hydrochloride (1.0 g, 5.1 mmol) in DMF (5 mL) was added Et3N (1.3 mL, 9.3 mmol). The mixture was heated at 85° C. for 16 hours. The reaction mixture was allowed to cool to room temperature, diluted with EtOAc (50 mL) and washed with H2O (50 mL×3). The organic layer was dried over sodium sulfate and concentrated. The resulting residue was purified by CombiFlash with 10% EtOAc in Hexane as the eluent to afford the desired 2-methyl-2-(2-nitro-phenylamino)-propionic acid tert-butyl ester (640 mg, 50%).

Workup

  1. temperatureto cool to room temperature
  2. washwashed with H2O (50 mL×3)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue was purified by CombiFlash with 10% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-a56a2960a3f54036a5b1cb5607203a81
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…