Ethyl bromoacetate → HCID 66879905, compound

HRID 1893539Notes

Reaction equation

HRID 1893539 reaction equation
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([CH3:14])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(N([CH2:30][CH3:31])C(C)C)(C)C>C(OCC)(=O)C>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][N:13]([CH2:7][C:6]([O:15][CH2:30][CH3:31])=[O:5])[C:10]1[CH:11]=[CH:12][C:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:15])=[CH:8][C:9]=1[CH3:14])[CH3:22]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 53432587tert-Butyl 4-amino-3-methylbenzoate

Product 1

HCID 66879905HCID 66879905, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

The compound (51.5 g) obtained in step B, ethyl bromoacetate (160 ml, 1.44 mol) and N,N-diisopropylethylamine (250 ml, 1.47 mol) were mixed, and the mixture was stirred with heating at 140° C. for 10 hr. The reaction mixture was cooled, diluted with ethyl acetate, and the organic layer was washed with 20% aqueous citric acid solution and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give a mixture of the title compound and N-(4-tert-butoxycarbonyl-2-methyl)phenylglycine ethyl ester. To this mixture were added ethyl bromoacetate (80 ml, 719 mmol) and N,N-diisopropylethylamine (125 ml, 735 mmol), and the mixture was stirred again with heating at 140° C. for 11 hr, which was followed by the purification similar to the above to give the title compound (95.3 g) as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washthe organic layer was washed with 20% aqueous citric acid solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe solution was concentrated under reduced pressure
  6. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)
  7. customto give

Sources & evidence

ORD record
ord-ec156923af8d43ba991138ed71fcf1e0
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

Loading…