2,6-Lutidine → 3-[(3,4-Dichloro-phenyl)-methoxycarbonylmethyl-amino]-propionic Acid tert-butyl ester

HRID 1096195Notes

Reaction equation

HRID 1096195 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22].N1C(C)=CC=CC=1C>CC#N>[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][N:9]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)[CH2:20][C:21]([O:23][CH3:24])=[O:22])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 60984Methyl bromoacetateHCID 667832463-(3,4-Dichloro-phenylamino)-propionic Acid tert-butyl ester

Product 1

HCID 667831343-[(3,4-Dichloro-phenyl)-methoxycarbonylmethyl-amino]-propionic Acid tert-butyl esterYield 71.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
115 °C

Procedure

A neat solution of 8.82 g (30.39 mmol) of 3-(3,4-dichloro-phenylamino)-propionic acid tert-butyl ester, 13.97 ml (151.97 mmol) of methyl bromoacetate and 17.64 ml (151.97 mmol) of 2,6-lutidine was stirred 14 h at 60° C., diluted with 20 ml of CH3CN and heated at 115° C. for 6 h. The reaction was then partitioned between aq. 10% KHSO4 solution and EtOAc (3×). The organic phases were washed with aq. 10% NaCl solution, dried over Na2SO4 evaporated and purified by flash silica gel column (n-heptane:EtOAc 95:5 to 9:1) to yield 7.86 g (71%) of the title compound as an yellow oil. MS: 362.0 (MH+, 2Cl).

Workup

  1. customThe reaction was then partitioned between aq. 10% KHSO4 solution and EtOAc (3×)
  2. washThe organic phases were washed with aq. 10% NaCl solution
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. custompurified by flash silica gel column (n-heptane:EtOAc 95:5 to 9:1)

Sources & evidence

ORD record
ord-626201a9e3994591ab0db9102f675838
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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