Ammonium Hydroxide → HCID 68535478, compound

HRID 2096132Notes

Reaction equation

HRID 2096132 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([N:15]([CH3:28])[C:16](=[O:27])[CH:17]([NH:25][CH3:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10]([O:12]CC)=O.[NH4+].[OH-]>C1COCC1>[CH2:18]([CH:17]1[N:25]([CH3:26])[C:10](=[O:12])[CH:9]([CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[I:1])[N:15]([CH3:28])[C:16]1=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 68537016HCID 68537016, compound

Product 1

HCID 68535478HCID 68535478, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(2-iodophenyl)-2-[methyl-(2-methylamino-3-phenylpropionyl)amino]propionate (2.1 g, 4.2 mmol) was taken up in THF (30 ml), and NH4OH (25% (w/v) in H2O, 20 ml) was added. The mixture was stirred at room temperature for 12 h and then concentrated on a rotary evaporator. The residue obtained in this manner was purified by column chromatography (SiO2, hexane/ethyl acetate). This gave 0.4 g (21%) of a non-polar isomer and 0.6 g (31%) of a polar isomer.

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. customThe residue obtained in this manner
  3. customwas purified by column chromatography (SiO2, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-62ec3f6e7b7a4480a873f5c74c92b03f
Source dataset
uspto-grants-2013_05
Patent number
US08450301B2

Reaction notes

Loading…