HCID 58481173, compound → HCID 58481118, compound

HRID 1625706Notes

Reaction equation

C([NH:4][C:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[C:19]([N+:26]([O-:28])=[O:27])[CH:18]=1)(C(OCC)=O)[C:6]([O:8]CC)=[O:7])(=O)C>Cl>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][CH:5]([NH2:4])[C:6]([OH:8])=[O:7])=[CH:18][C:19]=1[N+:26]([O-:28])=[O:27])(=[O:25])[CH3:24]

Participants

Conditions

Temperature: 100 °C

Procedure

Diethyl 2-acetamido-2-(4-acetyl-3-nitrobenzyl)malonate (2.0 g) was dissolved in 10 mL 37% HCl, heated at 100° C. overnight, and cooled down. The resulting solid was collect by filtration, affording 3-(4-acetyl-3-nitrophenyl)-2-aminopropanoic acid. 1H NMR (400 MHz, D2O): δ 8.01(s, 1H), 7.53 (d, J=7.6 Hz, 1H), 7.50 (d, J=7.6 Hz, 1H), 4.07 (m, 1H), 3.20-3.34 (m, 2H), 2.52 (s, 3H); 13C NMR: δ 201.39, 170.78, 174.89, 140.02, 137.84, 136.28, 129.59, 126.46, 54.46, 36.56, 30.01; ESI-MS (m/z) 253.22 (MH+).

Workup

temperaturecooled down
filtrationThe resulting solid was collect by filtration

Sources & evidence

ORD record: ord-9b2bfbc493a64377884235be574a38ab
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785151B2

Reaction notes

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