Water → Methyl 4-iodo-2-[(4-methoxy-4-oxobutanoyl)amino]benzoate

HRID 2387970Notes

Reaction equation

HRID 2387970 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([I:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CCN(C(C)C)C(C)C.[C:22]([CH2:26][CH2:27][C:28](Cl)=[O:29])([O:24][CH3:25])=[O:23].O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[I:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([NH:1][C:28](=[O:29])[CH2:27][CH2:26][C:22]([O:24][CH3:25])=[O:23])[CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 81531DiisopropylethylamineHCID 18929930Methyl 2-amino-4-iodobenzoate

Product 1

HCID 58476671Methyl 4-iodo-2-[(4-methoxy-4-oxobutanoyl)amino]benzoateYield 102.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-amino-4-iodobenzoate (17 g, 61.3 mmol) in DCM (200 mL), was added DIEA (10.6 mL, 64.4 mmol) and DMAP (37.5 mg, 0.31 mmol). To this solution was added 3-(carbomethoxy)propionyl chloride (8.3 mL, 67.4 mmol) dropwise, and the reaction mixture was allowed to stir at rt for 2 h. To the reaction mixture was then added H2O (80 mL) and the mixture was allowed to stir for 30 min. The organic solution was separated and the aqueous solution was extracted with DCM (2×100 mL). The organic solutions were combined, washed with H2O (2×100 mL) and brine (1×100 mL), dried over Na2SO4, filtered and concentrated to give methyl 4-iodo-2-[(4-methoxy-4-oxobutanoyl)amino]benzoate (24.6 g, 99%).

Workup

  1. stirringto stir for 30 min
  2. customThe organic solution was separated
  3. extractionthe aqueous solution was extracted with DCM (2×100 mL)
  4. washwashed with H2O (2×100 mL) and brine (1×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e96ee3e4af2940ea82cd7e432d54a515
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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