Hydrochloric Acid → HCID 57217095, compound

HRID 2082509Notes

Reaction equation

HRID 2082509 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]>>[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

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide2×HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 21460709HCID 21460709, compound

Product 1

HCID 57217095HCID 57217095, compound

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) and extract 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

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

Sources & evidence

ORD record
ord-2db7124870714717b3d6846bbe2e4e37
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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