Dichloromethane → Methyl 2-(4-ethoxy-4-oxobutanamido)-5-iodobenzoate

HRID 544979Notes

Reaction equation

HRID 544979 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(Cl)Cl.CCN(C(C)C)C(C)C.Cl[C:26](=[O:34])[CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>CN(C1C=CN=CC=1)C.O>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[C:9]([I:12])[CH:10]=[CH:11][C:2]=1[NH:1][C:26](=[O:34])[CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl esterHCID 847811Methyl 2-amino-5-iodobenzoate

Product 1

HCID 66935113Methyl 2-(4-ethoxy-4-oxobutanamido)-5-iodobenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

To methyl 2-amino-5-iodobenzoate (i-a) (15 g, 54 mmol) was added 200 mL of CH2Cl2, followed by DIEA (9.4 mL, 54 mmol) and a catalytic amount of DMAP. Ethyl 4-chloro-4-oxobutanoate (Rc═Rd═H) (8.5 mL, 60 mmol) was added, and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was then poured into 250 mL H2O, and the organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford ii-a (22 g, 99%) as a pale yellow solid: MS m/z=406 (M+H).

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto afford ii-a (22 g, 99%) as a pale yellow solid

Sources & evidence

ORD record
ord-a163bfd9748840959022c2bb5458f181
Source dataset
uspto-grants-2011_05
Patent number
US07935694B2

Reaction notes

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