Acetone → HCID 10989578, compound

HRID 1181018Notes

Reaction equation

[NH2:1][C@H:2]([C:7]([O:9]C)=[O:8])CC([O-])=O.[C:11]([O-])([O-])=[O:12].[Na+].[Na+].[C:17]1([CH2:23][CH2:24][C:25](Cl)=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl.C[C:30]([CH3:32])=[O:31]>O>[CH3:11][O:12][C:30](=[O:31])[CH2:32][CH:2]([NH:1][C:25](=[O:26])[CH2:24][CH2:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:7]([OH:9])=[O:8]

Participants

Conditions

Temperature: 5 °C

Procedure

Methyl L-aspartate (15.0 g, 0.082 mol), DI water (245 mL), acetone (20 mL), and Na2CO3 (30.8 g, 0.286 mol) were combined and cooled the solution to 5° C. The compound 3-phenyl-propionyl chloride (13.3 mL, 0.089 mol) was added dropwise via addition funnel over 10 min. The reaction was allowed to warm to ambient temperature and stir for 2 h. Conc. HCl (50 mL) was added to the thick slurry until the pH was ≦4.0. The reaction mixture was extracted with CH2Cl2 (3×100 mL). The combined organic layers were washed with water, dried (MgSO4), filtered, and concentrated. The clear, colorless oil was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.92 (br s, 1H), 7.28-7.17 (m, 5H), 6.57 (d, J=7.6 Hz, 1H), 4.87 (m, 1H), 3.67 (s, 3H), 2.96 (t, J=7.6 Hz, 2H), 2.89 (A of ABX, JAB=17.6 Hz, JAX=4.8 Hz, 1H), 2.88 (B of ABX, JBA=17.6 Hz, JBX=4.0 Hz, 1H), 2.69 (t, J=7.6 Hz, 2H); MS (EI+) 280 (M+H), 302 (M+H+Na).

Workup

temperatureto warm to ambient temperature
extractionThe reaction mixture was extracted with CH2Cl2 (3×100 mL)
washThe combined organic layers were washed with water
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe clear, colorless oil was used without further purification

Sources & evidence

ORD record: ord-6d8a0674653a4875b4d2d36ac08abc25
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282501B2

Reaction notes

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