Hydrochloric Acid → HCID 54708020, compound

HRID 970535Notes

Reaction equation

[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[H][H].[CH3:16][C:17]1[CH:28]=[CH:27][C:20]2[NH:21]C(=O)[O:23][C:24](=O)[C:19]=2[CH:18]=1.Cl>CC(N(C)C)=O>[CH2:6]([O:5][C:3]([C:2]1[C:1](=[O:9])[NH:21][C:20]2[C:19]([C:24]=1[OH:23])=[CH:18][C:17]([CH3:16])=[CH:28][CH:27]=2)=[O:4])[CH3:7]

Participants

Conditions

Temperature: 90 °C

Procedure

Neat diethyl malonate (18.05 g, 112.7 mmol) was added slowly to a suspension of sodium hydride (60% in mineral oil, 4.96 mg, 124 mmol) in dimethylacetamide under N2 atmosphere. The mixture was stirred at room temperature until the evolution of hydrogen gas ceased, then the mixture was heated to 90° C. for 30 min. then cooled to room temperature. A solution of Compound 11 (22 g, 124 mmol) in dimethylacetamide was added slowly and the solution heated overnight at 110° C. The mixture was cooled to room temperature, poured into ice water, and acidified by cold 10% HCl. The solids formed were filtered and washed several times by water to yield 10.2 g (36%) of white solids. M.P. 242° C. 1H NMR (DMSO-d6): δ 1.30 (t, J=7.2 Hz, 3H), 2.35 (s, 3H), 4.34 (q, J=7.2 Hz, 2H), 7.19 (d, J=8.4 Hz, 1H), 7.46 (dd, J=1.6, 8.4 Hz, 1H), 7.72 (d, J=1.6 Hz, 1H), 11.35 (s, 1H), 13.03 (s, 1H). EIMS m/z 248 (M+1).

Workup

temperaturethen cooled to room temperature
temperaturethe solution heated overnight at 110° C
temperatureThe mixture was cooled to room temperature
customThe solids formed
filtrationwere filtered
washwashed several times by water

Sources & evidence

ORD record: ord-cb5519e32fb44405975b92360bafbb14
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312220B2

Reaction notes

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