Ammonium Chloride → HCID 15341130, compound

HRID 1456298Notes

Reaction equation

HRID 1456298 reaction equation
C([Li])CCC.C(O[C:14]([NH:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[CH:20]2)=O)C1C=CC=CC=1.[C:27]([O:32][CH2:33][C@@H:34]1[O:36]C1)(=[O:31])CCC.[NH4+].[Cl-]>CCCCCC.C1COCC1.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[N:23]1[C:24]2[C:19](=[CH:18][C:17]([N:16]3[CH2:14][C@H:33]([CH2:34][OH:36])[O:32][C:27]3=[O:31])=[CH:26][CH:25]=2)[CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 54216864HCID 54216864, compoundHCID 178418339Butyllithium

Product 1

HCID 15341130HCID 15341130, compoundYield 45.2%

Reagents, catalysts & solvents 3

HCID 212261,10-Phenanthroline hydrateCatalystHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

4.70 ml (11.78 mmol) of a 2.5M solution of n-butyllithium in n-hexane are slowly added to a stirred solution, cooled to -78° C., of 3.28 g (11.78 mmol) of 6-benzyloxycarbonylamino-quinoline and 1 mg of 1,10-phenanthroline hydrate in 30 ml of anhydrous THF until the colour changes. Thereafter, 1.67 ml (11.78 mmol) of (R)-glycidyl butyrate are added dropwise and the reaction mixture is allowed to warm to room temperature in the course of 16 hours. 30 ml of saturated aqueous NH4Cl solution are then added dropwise in the course of 15 minutes. The aqueous phase is extracted with 3×60 ml of ethyl acetate and the organic phases are combined, washed with 2×50 ml of NaCl solution and dried over MgSO4. Evaporation of the solvent in vacuo, tritration of the residue with ether and recrystallization from 25 ml of ethanol gives 1.30 g (45%) of the title compound as colourless crystals.

Workup

  1. extractionThe aqueous phase is extracted with 3×60 ml of ethyl acetate
  2. washwashed with 2×50 ml of NaCl solution
  3. dry with materialdried over MgSO4
  4. customEvaporation of the solvent in vacuo, tritration of the residue
  5. customwith ether and recrystallization from 25 ml of ethanol

Sources & evidence

ORD record
ord-e8e4fc0780484420974d07d1f6b28fc3
Source dataset
uspto-grants-1998_12
Patent number
US05843967

Reaction notes

Loading…