Ammonium Chloride → HCID 15735660, compound

HRID 704611Notes

Reaction equation

HRID 704611 reaction equation
[CH:1]1(/[CH:7]=[C:8](\[CH2:12][P:13]([OH:19])([CH2:15][CH:16]([CH3:18])[CH3:17])=[O:14])/[C:9]([OH:11])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1CCN2C(=NCCC2)CC1.[C:31]([O:37][CH2:38]Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33].[Cl-].[NH4+]>CN(C)C=O.ClCCl.CO.C(O)(=O)C>[CH:1]1(/[CH:7]=[C:8](\[CH2:12][P:13]([OH:19])([CH2:15][CH:16]([CH3:17])[CH3:18])=[O:14])/[C:9]([O:11][CH2:38][O:37][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 87885Chloromethyl pivalateHCID 15735587HCID 15735587, compound

Product 1

HCID 15735660HCID 15735660, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21877243DCM MeOH AcOHSolvent

Procedure

To a solution of 100 mg (0.347 millimole) of (Z)-3-cyclohexyl-2-(hydroxyisobutylphosphinoyl)methylpropenoic acid in 1.0 ml of dimethylformamide were added 130 μl (0.87 millimole) of 1,8-diazabicyclo[5,4,0]-7-undecene and 75 μl (0.52 millimole) of chloromethyl pivalate, and the mixture was stirred at room temperature for 21 hours. Fifty milliliters of a saturated aqueous solution of ammonium chloride was added to the reaction mixture, and the mixture was extracted three times with 30 ml of ethyl acetate each time. The combined organic layers were washed with 10 ml of a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by preparative thin-layer chromatography silica gel 60 F254 made by E. Merck & Co.; dichloromethane/methanol/acetic acid [30:1:1)] to give 90 mg (yield 64%) of the captioned compound as a colorless oil.

Workup

  1. extractionthe mixture was extracted three times with 30 ml of ethyl acetate each time
  2. washThe combined organic layers were washed with 10 ml of a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by preparative thin-layer chromatography silica gel 60 F254

Sources & evidence

ORD record
ord-8556b961c32b43c797607a00d6d7b13e
Source dataset
uspto-grants-1991_01
Patent number
US04988681

Reaction notes

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