Hydrochloric Acid → HCID 57217095, compound

HRID 2396347Notes

Reaction equation

[H-].[Na+].[CH2:3]([NH:12][C:13]1[C:21]2[C:16](=[CH:17][C:18]([Cl:23])=[CH:19][C:20]=2[Cl:22])[N:15]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:14]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32])C(C1C=CC=CC=1)=O.[CH2:36](I)[CH3:37].Cl.CN(C)[CH:42]=[O:43]>C(OCC)(=O)C>[CH2:36]([CH2:37][CH2:3][NH:12][C:13]1[C:21]2[C:16](=[CH:17][C:18]([Cl:23])=[CH:19][C:20]=2[Cl:22])[N:15]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[C:14]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:42]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:43]

Participants

Conditions

Temperature: -10 °C

Procedure

Suspend sodium hydride (52 mg of a 60% dispersion, 1.73 mmol) in anhydrous dimethylformamide and cool to -10° C. Add, by dropwise addition, a solution of 3-[(phenacyl)amino]-2-carbethoxy-4,6-dichloro-1-tert-butyloxycarbonyl-indole (0.75 g, 1.57 mmol) in dimethylformamide. Stir under a nitrogen atmosphere for 30 minutes. Add ethyl iodide (0.27 g, 1.73 mmol) and stir at -10° C. for 5 hours. Pour into 1N hydrochloric acid (100 mL) andextract into ethyl acetate. Separate the organic phase and dry (MgSO4). Evaporate the solvent in vacuo and purify by flash chromatography (4:1 methylene chloride/ethyl acetate and recrystallize (ethyl acetate/hexane) to give the title compound; mp 110°-11° C.

Workup

additionAdd, by dropwise addition
customSeparate the organic phase
dry with materialdry (MgSO4)
customEvaporate the solvent in vacuo
custompurify by flash chromatography (4:1 methylene chloride/ethyl acetate
customrecrystallize (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-e3574c2ec13945578a48564c00644850
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05491153

Reaction notes

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