Hydrochloric Acid → HCID 54708020, compound

HRID 1767530Notes

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. 1HNMR (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-dcf25a1726a846f89fa9c4a624ed00cc
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235546B2

Reaction notes

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