Isatoic Anhydride → HCID 67138465, compound

HRID 1592035Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:24])[CH:4]([NH2:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1.[C:25]12[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=1)[NH:30]C(=O)O[C:26]2=[O:27]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:24])[CH:4]([NH:23][C:26](=[O:27])[C:25]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH2:30])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of the title G compound, 3-(3-benzyloxy-4-nitro-phenyl)-2-amino-propionic acid methyl ester (597 mg, 1.7 mmol), isatoic anhydride (278 mg, 1.7 mmol) and pyridine (5 mL) is heated with stirring at 80° C. for 7 h and allowed to cool to RT overnight. The mixture is evaporated to dryness, the residue is dissolved in EtOAc and the solution is washed with water and brine, dried over anhydrous MgSO4, filtered and evaporated. The residue is purified by chromatography (silica gel column, 3×20 cm, on EtOAc-hexane-methanol, 8:12:2) to give 2-(2-amino-benzoylamino)-3-(3-benzyloxy-4-nitro-phenyl)-propionic acid methyl ester: 1H-NMR δ 7.815 (d, 1H), 6.294 (s, 1H), 6.825 (d, 1H), 7.384-7.206 (m, 7H), 6.699-6.577 (m, 3H), 5.532 (br s, 2H), 5.093-5.039 (m, 3H), 3.749 s, 3H), 3.403-3.175 (m, 2H).

Workup

temperatureis heated
temperatureto cool to RT overnight
customThe mixture is evaporated to dryness
dissolutionthe residue is dissolved in EtOAc
washthe solution is washed with water and brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customevaporated
customThe residue is purified by chromatography (silica gel column, 3×20 cm, on EtOAc-hexane-methanol, 8:12:2)

Sources & evidence

ORD record: ord-3e60d261b4a44132891e9fdcb36fb9c4
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291635B2

Reaction notes

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