Hydrochloric Acid → HCID 19024829, compound

HRID 249173Notes

Reaction equation

HRID 249173 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:31]=[C:32]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH:33]=1)[C:12]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:15]=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:44]([C:48]1[CH:55]=[CH:54][C:51]([CH2:52]Cl)=[CH:50][CH:49]=1)[CH:45]([CH3:47])[CH3:46].Cl>CN(C)C=O.C(OCC)(=O)C>[CH2:44]([C:48]1[CH:55]=[CH:54][C:51]([CH2:52][N:34]([C:32]2[CH:31]=[C:11]([CH:10]=[C:9]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:52][C:51]3[CH:54]=[CH:55][C:48]([CH2:44][CH:45]([CH3:47])[CH3:46])=[CH:49][CH:50]=3)[CH:33]=2)[C:12]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:15]=2)=[O:13])[C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])=[CH:50][CH:49]=1)[CH:45]([CH3:47])[CH3:46]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1812891-(Chloromethyl)-4-(2-methylpropyl)benzeneHCID 19024802HCID 19024802, compound

Product 1

HCID 19024829HCID 19024829, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 4-[3-[3,5-bis[tertbutoxycarbonylamino)benzoyl]indol-1-yl]butyrate (300 mg) in N,N-dimethylformamide (5 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 54 mg) in N,N-dimethylformamide (5 ml) at 0° C. The mixture was stirred at 0° C. for 30 minutes, and a solution of 4-isobutylbenzyl chloride (388 mg) in N,N-dimethylformamide (5 ml) was added at 0° C. The reaction mixture was stirred at 0° C. for 3 hours, and poured into a mixture of 0.1N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water, aqueous solution of sodium bicarbonate and brine in successively. After dryness over magnesium sulfate and evaporation of the solvent, the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4) to give ethyl 4-[3-[3,5-bis[N-(4-isobutylbenzyl)-N-tert-butoxycarbonyl- amino]benzoyl]indol-1-yl]butyrate (155 mg) as an oil.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 3 hours
  2. customThe organic layer was separated
  3. washwashed with water, aqueous solution of sodium bicarbonate and brine in successively
  4. customAfter dryness over magnesium sulfate and evaporation of the solvent
  5. customthe residue was chromatographed on silica gel (25 g)
  6. washeluting with a mixture of ethyl acetate and hexane (1:4)

Sources & evidence

ORD record
ord-58c232b99e2d4968aff420f3c22481d8
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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