Ammonium Chloride → HCID 68907678, compound

HRID 546482Notes

Reaction equation

HRID 546482 reaction equation
C[Li].[C:3]([O:7][C:8]([NH:10][C@H:11]1[CH2:16][C@H:15](C(OCC)=O)[CH2:14][CH2:13][C@H:12]1[NH:22][C:23]([C:25]1[NH:26][C:27]2[C:32]([CH:33]=1)=[CH:31][C:30]([Cl:34])=[CH:29][CH:28]=2)=[O:24])=[O:9])([CH3:6])([CH3:5])[CH3:4].[Cl-].[NH4+]>O1CCCC1>[C:3]([O:7][C:8]([NH:10][C@H:11]1[CH2:16][C@H:15]([C:3]([OH:7])([CH3:5])[CH3:4])[CH2:14][CH2:13][C@H:12]1[NH:22][C:23]([C:25]1[NH:26][C:27]2[C:32]([CH:33]=1)=[CH:31][C:30]([Cl:34])=[CH:29][CH:28]=2)=[O:24])=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 67056493HCID 67056493, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 68907678HCID 68907678, compoundYield 118.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyllithium (1.14N solution, 2.27 ml) was added to a tetrahydrofuran solution (10 ml) of (1R*,2S*,4R*)-N2-tert-butoxycarbonyl-N1-[(5-chloroindol-2-yl)carbonyl]-4-ethoxycarbonyl-1,2-cyclohexanediamine (200 mg) at −78° C., and the mixture was stirred for 1 hour and then 2 hours under ice cooling. An aqueous solution of ammonium chloride was added to the reaction mixture to extract the reaction mixture with chloroform, and the resultant organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:3) to obtain the title compound (115 mg) as a colorless solid.

Workup

  1. custom2 hours
  2. extractionto extract the reaction mixture with chloroform
  3. washthe resultant organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-291db93d7f374011b2ab71f0d64a50f9
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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