Water → (7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-ylamino)-acetic acid methyl ester

HRID 643951Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[O:8][C:7](=[O:20])[C:6]([O:21][CH3:22])=[CH:5]2.C([O-])([O-])=O.[K+].[K+].Br[CH2:30][C:31]([O:33][CH3:34])=[O:32].O>CN(C=O)C>[CH3:34][O:33][C:31](=[O:32])[CH2:30][NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[O:8][C:7](=[O:20])[C:6]([O:21][CH3:22])=[CH:5]2

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 6-amino-7-benzyloxy-3-methoxychromen-2-one (0.880 g, 2.96 mmol) and K2CO3 (0.820 g, 5.92 mmol) in DMF (50 mL) is added methyl bromoacetate (0.36 mL, 3.85 mmol). The mixture is stirred at 60° C. for 3 h. Additional methyl bromoacetate (0.14 mL) is added, and after 3 h, the mixture is allowed to cool to ambient temperature and poured into water and extracted with EtOAc. The organic layer is washed with water (3×), sat. NaCl, and dried over sodium sulfate. The solvent is removed under reduced pressure and the residue purified by flash chromatography using hexanes/EtOAc (7:1) to afford (7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-ylamino)-acetic acid methyl ester as a yellow solid: 1H NMR (CDCl3) δ 7.44-7.33 (m, 5H), 6.79 (s, 1H), 6.75 (s, 1H), 6.36 (s, 1H), 5.13 (s, 2H), 3.95 (s, 2H), 3.85 (s, 3H), 3.77 (s, 3H); (M+H)+=370.

Workup

waitafter 3 h
temperatureto cool to ambient temperature
extractionextracted with EtOAc
washThe organic layer is washed with water (3×), sat. NaCl
dry with materialdried over sodium sulfate
customThe solvent is removed under reduced pressure
customthe residue purified by flash chromatography

Sources & evidence

ORD record: ord-e620a2114f4d4a749a41d16e9563d347
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700633B2

Reaction notes

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