Water → Ethyl 4-[2-(tert.-butoxycarbonyl-methoxy)-1-methyl-ethylamino]-3-chlorobenzoate

HRID 551257Notes

Reaction equation

HRID 551257 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[NH:13][CH:14]([CH3:17])[CH2:15][OH:16])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[H-].[Na+].Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].O>CN(C=O)C>[C:25]([O:24][C:22]([CH2:21][O:16][CH2:15][CH:14]([NH:13][C:12]1[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=1[Cl:1])[CH3:17])=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 67048695Ethyl 3-chloro-4-(2-hydroxy-1-methyl-ethylamino)-benzoate

Product 1

HCID 67049365Ethyl 4-[2-(tert.-butoxycarbonyl-methoxy)-1-methyl-ethylamino]-3-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.12 g (4.35 mmol) ethyl 3-chloro-4-(2-hydroxy-1-methyl-ethylamino)-benzoate are combined in 10 ml DMF with 0.21 g (4.78 mmol) 55% sodium hydride dispersion and stirred for 5 min at ambient temperature. Then 0.67 ml tert.-butyl bromoacetate are added and the mixture is stirred for a further 16 h at ambient temperature. Then the reaction mixture is poured into water and extracted with ethyl acetate. The combined organic phases are washed with water and sat. sodium chloride solution, dried over sodium sulphate and evaporated down completely i. vac. The residue is purified by chromatography on silica gel (eluting gradient: petroleum ether/ethyl acetate=95:5→80:20)

Workup

  1. stirringthe mixture is stirred for a further 16 h at ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases are washed with water and sat. sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated down completely
  6. customThe residue is purified by chromatography on silica gel (eluting gradient: petroleum ether/ethyl acetate=95:5→80:20)

Sources & evidence

ORD record
ord-63308ee9534b490988dcb0034e87528d
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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