Water → HCID 117776421, compound

HRID 1497553Notes

Reaction equation

HRID 1497553 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:6]=[C:7]([CH:15]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH2:23]([NH2:25])[CH3:24].O.C(OCC)(=O)C>O1CCCC1>[CH2:23]([NH:25][CH2:2][C:3]1[CH:4]=[C:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:6]=[C:7]([CH:15]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6341EthylamineHCID 8857Ethyl AcetateHCID 90282074HCID 90282074, compound

Product 1

HCID 117776421HCID 117776421, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of di-tert-butyl 5-(bromomethyl)isophthalate (1.00 g) in tetrahydrofuran (10.0 mL) were added a 70% aqueous ethylamine solution (2.21 mL), followed by stirring at room temperature overnight. To the reaction mixture were added water and ethyl acetate, and the organic layer was extracted. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate, and subsequently chloroform-methanol) to obtain di-tert-butyl 5-[ethylamino(methyl)]isophthalate (558 mg).

Workup

  1. extractionthe organic layer was extracted
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate, and subsequently chloroform-methanol)

Sources & evidence

ORD record
ord-2840977c6c604c7aacd660bf1c650db7
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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