Diisopropylethylamine → Methyl 4-(2-methoxy-2-oxo-1-phenylethylamino)-3-nitrobenzoate

HRID 2205096Notes

Reaction equation

HRID 2205096 reaction equation
Cl.[NH2:2][CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].F[C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:7][O:6][C:4](=[O:5])[CH:3]([NH:2][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5219721Methyl 4-fluoro-3-nitrobenzoateHCID 12247454Methyl 2-amino-2-phenylacetate hydrochloride

Product 1

HCID 67980137Methyl 4-(2-methoxy-2-oxo-1-phenylethylamino)-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2-amino-2-phenylacetate hydrochloride (500 mg, 2.48 mmol, 1.00 equiv) in DMF (5 mL), methyl 4-fluoro-3-nitrobenzoate (1.0 g, 5.03 mmol, 2.00 equiv), and DIEA (1 g, 7.75 mmol, 3.13 equiv) were combined in a 50-mL round-bottom flask and allowed to react, with stifling, overnight at room temperature. The reaction was then quenched by the addition of 100 mL of water. The solids were collected by filtration, resulting in 0.9 g (crude) of methyl 4-(2-methoxy-2-oxo-1-phenylethylamino)-3-nitrobenzoate as a yellow solid.

Workup

  1. customto react
  2. customovernight
  3. customat room temperature
  4. customThe reaction was then quenched by the addition of 100 mL of water
  5. filtrationThe solids were collected by filtration
  6. customresulting in 0.9 g (crude) of methyl 4-(2-methoxy-2-oxo-1-phenylethylamino)-3-nitrobenzoate as a yellow solid

Sources & evidence

ORD record
ord-327bf225b101464e9899538372444e81
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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