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

HRID 544979Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 544979
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a163bfd9748840959022c2bb5458f181
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935694B2

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