Diethyl Ether → HCID 22612281, compound

HRID 844052Notes

Reaction equation

HRID 844052 reaction equation
C(OC([CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][NH:13][C:14]([C:16]2[C:17]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:15])[CH2:8][CH2:7]1)=O)C.[CH3:30][Li].C([O:34][CH2:35][CH3:36])C>O1CCCC1>[Cl:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[O:22][C:17]1[N:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]([NH:13][CH2:12][CH:9]1[CH2:10][CH2:11][CH:6]([C:35]([OH:34])([CH3:36])[CH3:30])[CH2:7][CH2:8]1)=[O:15]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 53846191HCID 53846191, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 22612281HCID 22612281, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a 4-({[2-(3-Chloro-phenoxy)-pyridine-3-carbonyl]-amino}-methyl)-cyclohexanecarboxylic acid ethyl ester (0.220 grams, 0.53 mmole) in tetrahydrofuran (5 ml) at −78° C. 1.4 M methyl lithium in diethyl ether (1.13 ml, 1.58 mmole) was added dropwise to keep the temperature below −60° C. and stirred at −78° C. for 2 hours and allowed to warm to room temperature. The mixture was quenched with sat'd NH4Cl and extracted with ethyl acetate. The combined organics were washed with water and brine, dried over Na2SO4, filtered and concentrated to a product which was purified by chromatography on silica eluting with 2/3 ethyl acetate/hexane to give an off-white oil. (0.040 g); 1H NMR (400 mhz, CDCl3) d 0.84-1.70 (m, 12H), 1.83-1.87 (m, 4H), 3.30-3.37 (m, 2H), 7.04-7.07 (m, 1H), 7.11-7.19 (m, 2H), 7.24-7.27 (m, 1H), 7.35-7.39 (m, 1H), 7.79 (bs, 1H),8.19-8.21 (m, 1H), 8.60-8.62 (m, 1H).

Workup

  1. customat −78° C
  2. customthe temperature below −60° C.
  3. temperatureto warm to room temperature
  4. customThe mixture was quenched with sat'd NH4Cl
  5. extractionextracted with ethyl acetate
  6. washThe combined organics were washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to a product which
  10. customwas purified by chromatography on silica eluting with 2/3 ethyl acetate/hexane
  11. customto give an off-white oil

Sources & evidence

ORD record
ord-4705a4409fca4989874614d080e688d0
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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