Indole-3-Acetic Acid → HCID 68277836, compound

HRID 929437Notes

Reaction equation

HRID 929437 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([OH:13])=O)=[CH:2]1.[CH:14]([N:17]=[C:18]=[N:19][CH:20]([CH3:22])[CH3:21])([CH3:16])[CH3:15].CN(C=[O:27])C>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([N:17]([CH:14]([CH3:16])[CH3:15])[C:18](=[O:27])[NH:19][CH:20]([CH3:22])[CH3:21])=[O:13])=[CH:2]1

Participants

4

Reactant 3

HCID 802Indole-3-Acetic AcidHCID 6228DimethylformamideHCID 12734Diisopropylcarbodiimide

Product 1

HCID 68277836HCID 68277836, compoundYield 60%

Procedure

To 87.5 mg (0.5 mM) of 3-indolylacetic acid dissolved in dry DMF was added 79 ul (0.5 mM) N,N′-diisopropyl carbodiimide and the mixture was stirred overnight at RT. The solvent was evaporated, the residue was triturated with dry diethyl ether and the crystals formed from DIU were filtered. The flash chromatography from CHCl3 and CHCl3/MeOH 99/1 yielded 91 mg light yellow oil (60%) with Rf=0.82 (CHCl3/MeOH 9/1). The observed mass by LC/MS was 302 for [M+H]+, corresponding to the expected mass of 301.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with dry diethyl ether
  3. customthe crystals formed from DIU
  4. filtrationwere filtered

Sources & evidence

ORD record
ord-281bbe44d14643109e186b4f7a12cb49
Source dataset
uspto-grants-2016_03
Patent number
US09296691B2

Reaction notes

Loading…