Triethylamine → HCID 15101124, compound

HRID 704592Notes

Reaction equation

HRID 704592 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([OH:11])=O)[CH2:4][CH2:3]1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[C:27]1([C@@H:33]([NH2:35])[CH3:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([CH2:8][C:9]([NH:35][C@H:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH3:34])=[O:11])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 758181-Phenethylamine, (-)-HCID 99204382-(4-oxocyclohexyl)acetic Acid

Product 1

HCID 15101124HCID 15101124, compoundYield 143.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-oxocyclohexaneacetic acid (28.39 g) (Example H) and triethylamine (30.4 ml) in 800 ml of dichloromethane at -10° C. is treated dropwise with isobutyl chloroformate (26.0 ml). The reaction mixture is stirred at this temperature for 15 minutes and 1(S)-phenylethylamine (26.51 g) is added via syringe. After 30 minutes at -10° C., the mixture is stirred at room temperature for another 30 minutes. The reaction is concentrated in vacuo and the residue partitioned between ethyl acetate (1000 ml) and 1 N hydrochloric acid solution (400 ml). The organic extract is washed with 1 N sodium hydroxide solution and brine, dried (magnesium sulfate), and concentrated in vacuo to leave 67.5 g of crude (S)-4-oxo-N-(1-phenylethyl)cyclohexaneacetamide as a white solid; mp 110°-151° C.

Workup

  1. waitAfter 30 minutes at -10° C.
  2. stirringthe mixture is stirred at room temperature for another 30 minutes
  3. concentrationThe reaction is concentrated in vacuo
  4. customthe residue partitioned between ethyl acetate (1000 ml) and 1 N hydrochloric acid solution (400 ml)
  5. extractionThe organic extract
  6. washis washed with 1 N sodium hydroxide solution and brine
  7. dry with materialdried (magnesium sulfate)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53f90297b01344a3ac10c331ebf78d36
Source dataset
uspto-grants-1991_01
Patent number
US04988699

Reaction notes

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