Glycine → HCID 66713023, compound

HRID 1406170Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])O[C:5]2=[O:12].[NH2:13][CH2:14][C:15]([OH:17])=[O:16].S([O-])(O[CH3:22])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[CH3:22][O:16][C:15](=[O:17])[CH2:14][N:13]1[C:5](=[O:12])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[C:7]1=[O:11]

Participants

Conditions

Temperature: 210 °C

Procedure

A solid mixture of 5-fluoro-isobenzofuran-1,3-dione (3.68 g, 22.15 mmol) and glycine (1.66 g, 22.15 mmol) was stirred at 200-220° C. for 5 min. After cooling, it was dissolved in 25 ml of acetone. Methyl sulfate (4.19 g, 33.23 mmol) and potassium carbonate (4.59 g, 33.23 mmol) was added. The mixture was stirred at reflux for 2 h. After cooling, it was diluted with 100 ml of ethyl acetate. Insoluble was filtered off and filtrate was concentrated. Residue was taken into 200 ml of ethyl acetate and washed with water and brine. Ethyl acetate layer was dried over sodium sulfate, filtered, and concentrated to give 5.1 g of product. 1H NMR (200 MHz, CDCl3) δ 7.88 (dd, J=8.2, 4.3 Hz, 1 H), 7.54 (dd, J=6.8, 2.2 Hz, 1 H), 7.40 (m, 1 H), 4.44 (s, 2 H), 3.77 (s, 3 H).

Workup

temperatureAfter cooling
stirringThe mixture was stirred
temperatureat reflux for 2 h
temperatureAfter cooling
filtrationInsoluble was filtered off
concentrationfiltrate was concentrated
washwashed with water and brine
dry with materialEthyl acetate layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-771fe122a8044bcca74e44ef2fd01b4f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916585B2

Reaction notes

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