Indole → HCID 68176377, compound

HRID 408617Notes

Reaction equation

HRID 408617 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH3:12][O:13][C:14](=[O:37])[CH2:15][CH2:16][CH2:17][N:18]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[C:19]([C:21]1([CH3:28])[CH2:24][CH2:23][N:22]1[C:25](Cl)=[O:26])=[O:20]>C1COCC1>[CH3:12][O:13][C:14](=[O:37])[CH2:15][CH2:16][CH2:17][N:18]([CH2:29][C:30]1[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=1)[C:19]([C:21]1([CH3:28])[CH2:24][CH2:23][N:22]1[C:25]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)=[O:26])=[O:20]

Participants

5

Reactant 3

HCID 798IndoleHCID 24758Sodium hydrideHCID 86702031HCID 86702031, compound

Product 1

HCID 68176377HCID 68176377, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of indole (1 eq.) in THF is added NaH (1.5 eq., 60% in oil) and the mixture is stirred at 20° C. for 1 h. A solution of 4-[(4-Chloro-benzyl)-(1-chlorocarbonyl-2-methyl-azetidine-2-carbonyl)-amino]-butyric acid methyl ester in THF in added dropwise and the mixture is stirred at 20° C. for 16 h. The mixture was concentrated and the residue dissolved in EtOAc, washed with aqueous HCl (0.1N), a saturated aqueous solution of NaHCO3 and brine. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue is used as such in next step.

Workup

  1. stirringthe mixture is stirred at 20° C. for 16 h
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue dissolved in EtOAc
  4. washwashed with aqueous HCl (0.1N)
  5. dry with materialThe organic layer is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b60265b0d6754cedbd67f0f08a1ff394
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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