1,2-Dichloroethane → [(4-Iodo-benzoyl)-methoxycarbonylmethyl-amino]-acetic acid methyl ester

HRID 1786832Notes

Reaction equation

Cl.[CH3:2][O:3][C:4](=[O:12])[CH2:5][NH:6][CH2:7][C:8]([O:10][CH3:11])=[O:9].CN1CCOCC1.[I:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[CH3:11][O:10][C:8](=[O:9])[CH2:7][N:6]([C:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:21]([I:20])=[CH:22][CH:23]=1)[CH2:5][C:4]([O:3][CH3:2])=[O:12]

Participants

Conditions

Temperature: 45 °C

Procedure

Iminodiacetic dimethyl ester hydrochloride (624 mg, 3.24 mmol) was suspended in 5 mL of anhydrous DMF under nitrogen, and N-methylmorpholine (360 μL, 3.27 mmol) was added. After 5 minutes, 4-iodobenzoic acid (805 mg, 3.25 mmol) was added, followed by HOBt (450 mg, 3.33 mmol) and EDC (1.0 g, 5.28 mmol). The reaction was stirred overnight at 45° C. The solvent was removed and the residue was dissolved in EtOAc (20 mL) and washed with 0.5 M HCl, sat. NaHCO3 and water. The organic phase was collected, the solvent removed and the mixture purified by column chromatography (silica; hexanes:EtOAc 90:10-65:45), yielding the product as a white solid. MS (ES+): Cal'd. 392.00 (MH+), exp. 391.98 (MH+).

Workup

customThe solvent was removed
dissolutionthe residue was dissolved in EtOAc (20 mL)
washwashed with 0.5 M HCl, sat. NaHCO3 and water
customThe organic phase was collected
customthe solvent removed
customthe mixture purified by column chromatography (silica; hexanes:EtOAc 90:10-65:45)

Sources & evidence

ORD record: ord-b67afd606d3b436baa6c2aaa974b0356
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507858B2

Reaction notes

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