Diethyl Ether → HCID 70564665, compound

HRID 1427261Notes

Reaction equation

HRID 1427261 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)([CH2:23][CH3:24])[C:19](OC)=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:32]([Mg]Br)[CH3:33].CCOCC.C(=O)(O)[O-].[Na+]>C1COCC1.CC(=O)OCC.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([C:18]([N:13]2[C:14]3[C:10](=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:12]2)([C:19]2([OH:20])[CH2:33][CH2:32]2)[CH2:23][CH3:24])=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 70560825HCID 70560825, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 70564665HCID 70564665, compound

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-{4-[(tert-butoxycarbonyl)amino]-1H-indol-1-yl}-2-(4-chlorophenyl)butanoate (0.44 g, 1 mmol), as described in Example 3 step A, in THF (20 mL) was added titanium (IV) isopropoxide (0.3 g, 1 mmol) and the solution was cooled to 0° C. Ethylmagnesium bromide 3 N in ether (1.8 mL, 5 mmol) was then added via syringe pump over 1 hr period and the reaction was stirred for an additional 30 min at this temperature. The mixture was warmed into RT and stirred over night. The final mixture was diluted with EA, treated with saturated sodium bicarbonate solution, extracted with EA and DCM, dried over sodium sulfate and concentrated. The residue was purified by flash-chromatography over silica gel (eluted with hexanes/EA 95:5 to EA) to give the title compound. LC/MS m/z=441.0[M+H]+.

Workup

  1. temperatureThe mixture was warmed into RT
  2. stirringstirred over night
  3. extractionextracted with EA and DCM
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash-chromatography over silica gel (eluted with hexanes/EA 95:5 to EA)

Sources & evidence

ORD record
ord-30d4db862ee84c28abe4bb94299fa929
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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