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

HRID 2373354Notes

Reaction equation

HRID 2373354 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 MgSO41 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. customdried over MgSO41
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto afford ii-a (22 g, 99%) as a pale yellow solid

Sources & evidence

ORD record
ord-e1fa55b1b9214d6693a9b865f125fdf1
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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