Hexane → HCID 58822050, compound

HRID 546481Notes

Reaction equation

HRID 546481 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][C@@H:13]([C:15](OCC)=[O:16])[CH2:12][CH2:11][C@H:10]1[NH:20][C:21]([C:23]1[NH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][C:28]([Cl:32])=[CH:27][CH:26]=2)=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCCCC.[H-].C([Li])C(C)C.[Cl-].[NH4+]>ClCCl>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][C@@H:13]([CH2:15][OH:16])[CH2:12][CH2:11][C@H:10]1[NH:20][C:21]([C:23]1[NH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][C:28]([Cl:32])=[CH:27][CH:26]=2)=[O:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 58822150HCID 58822150, compoundHCID 178506454HCID 178506454, compound

Product 1

HCID 58822050HCID 58822050, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1R*,2R*,4S*)-N2-(tert-Butoxycarbonyl)-N1-[(5-chloroindol-2-yl)carbonyl]-4-ethoxycarbonyl-1,2-cyclohexanediamine (735 mg) was dissolved in dichloromethane (10 ml), a 1N hexane solution (5 ml) of isobutyllithium hydride was added at −78° C., and the mixture was stirred for 3 hours and then 30 minutes at 0° C. A saturated aqueous solution of ammonium chloride was added at −78° C., the mixture was extracted with dichloromethane, and the resultant organic layer was washed with a saturated aqueous solution of sodium bicarbonate and 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 (dichloromethane:methanol=19:1) to obtain the title compound (480 mg) as a colorless solid.

Workup

  1. custom30 minutes
  2. customat 0° C
  3. extractionthe mixture was extracted with dichloromethane
  4. washthe resultant organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (dichloromethane:methanol=19:1)

Sources & evidence

ORD record
ord-64f902739e28439a8c4f60fa62e01ea8
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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