Triethylamine → HCID 178501049, compound

HRID 221338Notes

Reaction equation

HRID 221338 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([OH:13])=O)[CH2:7][CH2:6]1)=[O:4].C([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])C.[CH2:21](OC(Cl)=O)C(C)C.O[NH:30][C:31](=[NH:38])C1C=CN=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]2[O:13][N:38]=[C:31]([C:19]3[CH:20]=[CH:21][CH:18]=[CH:17][N:16]=3)[N:30]=2)[CH2:9][CH2:10]1)=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 2968504-(Methoxycarbonyl)cyclohexane-1-carboxylic acidHCID 178513374HCID 178513374, compound

Product 1

HCID 178501049HCID 178501049, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of cyclohexane-1,4-dicarboxylic acid monomethyl ester (1.053 g, 5.66 mmol) and triethylamine (800 μl, 5.66 mmol) in toluene (30 ml) was cooled to 0° C. and isobutylchloroformate (735 μl, 5.66 mmol) introduced dropwise. The mixture was stirred at rt for 30 min whereupon activated, powdered 3 Å molecular sieves (5 g) and N-hydroxyisonicotinamidine (705 mg, 5.14 mmol) were added. The mixture was heated under reflux for 18 h, cooled and filtered through celite. The solvent was removed in vacuo and the residue purified by flash chromatography (IH-EtOAc, 1:1) to afford the title compound: RT=3.20 min; m/z (ES−)=288.2 [M+H]+.

Workup

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 18 h
  4. temperaturecooled
  5. filtrationfiltered through celite
  6. customThe solvent was removed in vacuo
  7. customthe residue purified by flash chromatography (IH-EtOAc, 1:1)

Sources & evidence

ORD record
ord-b048ea71b6644fc1a19ea909b0be6e18
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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