Hydrochloric Acid → HCID 15750463, compound

HRID 403531Notes

Reaction equation

C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:15])[CH:12]([Cl:14])[CH3:13].[Li+].[OH-].O.Cl>C1COCC1.CCOC(C)=O>[Cl:14][CH:12]([CH3:13])[C:11]([NH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:16])=[O:2])=[O:15]

Participants

Conditions

Temperature: 50 °C

Procedure

To the 2-(2-chloro-propionylamino)-benzoic acid methyl ester (7.75 g, 32.1 mmol) stirring in THF (40 mL) was added 1M LiOH/H2O (40 mL). The reaction was allowed to stir at 50° C. for 3 h. After this period the reaction was concentrated under vacuum to afford a crude residue that was acidified with 1N HCl. The resulting suspension was then diluted with EtOAc and washed with water (3×50 mL). The organic layer was then washed with brine (25 mL), dried over MgSO4, and concentrated under vacuum to afford crude acid. The crude material was purified by flash chromatography (silica gel, 80% EtOAc/Hex) to afford the desired product as an off white solid (7.1 g, 97% yield). 1H-NMR (CDCl3): δ 8.6 (d, 1H), 8.12 (d, 1H), 7.61 (t, 1H), 7.57 (t, 1H), 4.89 (br, 1H), 4.65 (t, 1H), 1.78 (d, 3H).

Workup

concentrationAfter this period the reaction was concentrated under vacuum
customto afford a crude residue that
washwashed with water (3×50 mL)
washThe organic layer was then washed with brine (25 mL)
dry with materialdried over MgSO4
concentrationconcentrated under vacuum
customto afford crude acid
customThe crude material was purified by flash chromatography (silica gel, 80% EtOAc/Hex)

Sources & evidence

ORD record: ord-e44296f786a948bfb4fde84229c1472b
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748440B2

Reaction notes

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