Ammonium Chloride → HCID 22254170, compound

HRID 1611719Notes

Reaction equation

HRID 1611719 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[CH:17]1[C:22](=[C:23]=[O:24])[CH:21]=[CH:20][C:19]([NH:25][CH2:26][CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:18]1.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O.O>[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[C:17]1[CH:18]=[C:19]([NH:25][CH2:26][CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:20]=[CH:21][C:22]=1[CH:23]([OH:24])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 131725264HCID 131725264, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 22254170HCID 22254170, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phenylmagnesiumbromide (1M in THF) (2eq) is added to a solution of 8 (50 mg) in THF (10 ml) at 78° C. under argon with stirring. The reaction is allowed to stir for 15 min. at 78° C. after the addition of Grignard at which time sat; aq. NH4Cl (4 ml) is added to quench the reaction. The mixture is diluted with EtOAc (60 ml) and water (2 ml), and the layers are separated. The organic layer is washed with sat. aq. NH4Cl (10 ml), water (10 ml), brine (10 ml), dried (Na2SO4), filtered and concentrated. The residue is purified by silica column chromatography eluting with EtOAc/hexane to give 13.

Workup

  1. stirringto stir for 15 min. at 78° C.
  2. additionafter the addition of Grignard at which time
  3. customto quench
  4. customthe reaction
  5. customthe layers are separated
  6. washThe organic layer is washed with sat. aq. NH4Cl (10 ml), water (10 ml), brine (10 ml)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue is purified by silica column chromatography
  11. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-dce057c42b7e426a84f1ad480725696e
Source dataset
uspto-grants-2006_01
Patent number
US06989382B2

Reaction notes

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