Ammonium Chloride → HCID 67110386, compound

HRID 2080675Notes

Reaction equation

HRID 2080675 reaction equation
[CH3:1][Mg]Br.[CH2:4]([S:6]([C:9]1[CH:37]=[CH:36][C:12]([O:13][C:14]2[C:28]([CH2:29][C:30](N(OC)C)=[O:31])=[CH:27][C:17]3[NH:18][C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[N:20][C:16]=3[CH:15]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:5].[Cl-].[NH4+]>O1CCCC1>[CH2:4]([S:6]([C:9]1[CH:37]=[CH:36][C:12]([O:13][C:14]2[C:28]([CH2:29][C:30]([CH3:1])=[O:31])=[CH:27][C:17]3[NH:18][C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[N:20][C:16]=3[CH:15]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86620339HCID 86620339, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 67110386HCID 67110386, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

With cooling with ice, 14 μl of a tetrahydrofuran solution of 3.0 M methylmagnesium bromide was added to a tetrahydrofuran (500 μl) solution of 8.7 mg of the compound obtained from Example 138, and stirred at room temperature for 30 minutes. then, 14 μl of a tetrahydrofuran solution of 3.0 M methylmagnesium bromide was added to it, and stirred at room temperature for 5 minutes. With cooling with ice, aqueous saturated ammonium chloride solution was added to it, extracted with chloroform, and the organic layer was washed with saturated saline water. After dried, the solvent was evaporated away under reduced pressure, and the residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=20/1) to obtain 4.0 mg of the entitled compound.

Workup

  1. stirringstirred at room temperature for 5 minutes
  2. additionwas added to it
  3. extractionextracted with chloroform
  4. washthe organic layer was washed with saturated saline water
  5. customAfter dried
  6. customthe solvent was evaporated away under reduced pressure
  7. customthe residue was purified
  8. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-df26e8dff0ca4154be9d851e697dc9d1
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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