Diazomethane → Methyl 3-[N-(p-chlorobenzyl)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate

HRID 1590105Notes

Reaction equation

HRID 1590105 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:17][C:18]([CH3:23])([CH3:22])[C:19]([OH:21])=[O:20])=[CH:4][CH:3]=1.[N+](=[CH2:28])=[N-]>CCOCC>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:17][C:18]([CH3:23])([CH3:22])[C:19]([O:21][CH3:28])=[O:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 108720243-[1-(4-Chlorobenzyl)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoic acid

Product 1

HCID 14980565Methyl 3-[N-(p-chlorobenzyl)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The acid from Step 1 (0.84 g) was dissolved in 10 mL of Et2O and a solution of diazomethane in Et2O was added portionwise until all the acid had been consumed. Excess diazomethane was removed by addition of 1 mL HOAc, the solvent was then removed and the residue chromatographed (hexane/EtOAc 4:1) to give the title compound.

Workup

  1. customhad been consumed
  2. customExcess diazomethane was removed by addition of 1 mL HOAc
  3. customthe solvent was then removed
  4. customthe residue chromatographed (hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-fb8d907e0fcb46d598d3dac88018553e
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

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