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

HRID 1403292Notes

Reaction equation

HRID 1403292 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-nitrobenzoateYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 2-amino-2-phenylacetate hydrochloride (2.5 g, 12.38 mmol, 1.00 equiv) in DMF (30 mL), methyl 4-fluoro-3-nitrobenzoate (5 g, 25.13 mmol, 2.00 equiv), and DIEA (5 g, 38.76 mmol, 3.13 equiv) was reacted overnight at 30° C. in a 100-mL round-bottom flask. The reaction was then quenched by the addition of 200 mL of water, and the solids were collected by filtration. Purification via silica gel column (petroleum ether/EtOAc (50:1)) yielded 3.82 g (90%) of methyl 4-(2-methoxy-2-oxo-1-phenylethylamino)-3-nitrobenzoate as a yellow solid. LC-MS (ES, m/z): 345 [M+H]+.

Workup

  1. customThe reaction was then quenched by the addition of 200 mL of water
  2. filtrationthe solids were collected by filtration
  3. customPurification via silica gel column (petroleum ether/EtOAc (50:1))

Sources & evidence

ORD record
ord-9f29c38cd59a40a7ae1ca6a4bdbc3aac
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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