Hydrochloric Acid → HCID 10382223, compound

HRID 277698Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=O)[N:8]([C@@H:11]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6](=[O:7])[C:5]2=[CH:24][CH:25]=1.Cl>C(O)C.[Zn]>[NH2:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:24][CH:25]=1)[C:6](=[O:7])[N:8]([C@@H:11]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9]2

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of diethyl (S)-2-(4-aminophthalimido)glutarate (10.5 g, 30.2 mmol) in ethanol (150 ml) was cooled in an acetonitrile/CO2 bath. Concentrated HCl (25 ml) was added followed by 30 mesh granular Zn (10.5 g, 0.161 mole) (Fisher) when the internal temperature has reached −40° C. The reaction mixure was stirred 1.5 hours at this temperature and a further 1 hour at −10° C. The excess of Zn was filtered from the solution, 10% palladium on carbon (1.0 g) was added, and the solution shaken under hydrogen at (30-50 psi) overnight. The catalyst was removed by filtration through celite and the filtrate concentrated in vacuo. The residue was absorbed onto silica gel (15 g) and purified by chromatography on silica gel (440 g) eluting with ethyl acetate:methylene chloride (1:14 g).

Workup

customhas reached −40° C
filtrationThe excess of Zn was filtered from the solution, 10% palladium on carbon (1.0 g)
additionwas added
stirringthe solution shaken under hydrogen at (30-50 psi) overnight
customThe catalyst was removed by filtration through celite
concentrationthe filtrate concentrated in vacuo
customThe residue was absorbed onto silica gel (15 g)
custompurified by chromatography on silica gel (440 g)
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-530b0d2e979c45578f221fdea2522585
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358952B1

Reaction notes

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