Phthalamic acid → N'-(1-Carbamoyl-1,2-dimethylpropyl)-N,N-diethyl-3,4-(methylenedioxy)phthalamide

HRID 1646444

Reaction equation

[C:1]([OH:12])(=O)[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([NH2:6])=[O:5].Cl[C:14]([O:16]CC)=[O:15].C([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])C.[CH3:26][C@@:27]([C:32]([NH2:34])=[O:33])([CH:29]([CH3:31])[CH3:30])N>O1CCCC1.O>[C:32]([C:27]([NH:6][C:4](=[O:5])[C:3]1[C:2](=[CH:10][CH:9]=[C:8]2[O:16][CH2:14][O:15][C:7]=12)[C:1]([N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])=[O:12])([CH3:26])[CH:29]([CH3:31])[CH3:30])(=[O:33])[NH2:34]

Participants

Conditions

Temperature: 10 °C

Procedure

A solution of N,N-diethyl-5,6-)methylenedioxy)phthalamic acid (3.00 g, 11.0 mmol) in tetrahydrofuran, under nitrogen at room temperature is treated with ethyl chloroformate (1.10 mL, 11.0 mmol), cooled to 10° C., treated with triethylamine (1.70 mL, 12.0 mmol), stirred for 30 minutes at 10° C., treated dropwise with a solution of α-methylvalinamide (1.43 g, 11.0 mmol) in tetrahydrofuran, stirred overnight at ambient temperatures, treated with water and concentrated in vacuo. The aqueous residue is extracted with ethyl acetate; the extracts are combined, washed with brine and saturated sodium bicarbonate, dried (MgSO4), and concentrated in vacuo to afford the title product as an amber foam 3.10 g (74.7%), identified by NMR and mass spectral analysis.

Workup

stirringstirred overnight at ambient temperatures
concentrationconcentrated in vacuo
extractionThe aqueous residue is extracted with ethyl acetate
washwashed with brine and saturated sodium bicarbonate
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0353ecbbe0dc4ae2a8d79fc0ded84164
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05180419

Linked notes

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