Triethylamine → HCID 9921977, compound

HRID 2229439Notes

Reaction equation

HRID 2229439 reaction equation
Cl[C:2](OCC)=O.[NH2:7][CH2:8][C:9]1([C:20]2([OH:25])[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:19]2[C:11](=[CH:12][C:13]3[S:17][CH:16]=[CH:15][C:14]=3[CH:18]=2)[CH2:10]1.C(N(CC)CC)C>ClCCl>[CH3:2][NH:7][CH2:8][C:9]1([C:20]2([OH:25])[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:19]2[C:11](=[CH:12][C:13]3[S:17][CH:16]=[CH:15][C:14]=3[CH:18]=2)[CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 18467753HCID 18467753, compound

Product 1

HCID 9921977HCID 9921977, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.29 ml of ethyl chloroformate in 40 ml of dichloromethane is introduced, at 0° C., to a mixture of 1 g of the product of Example 21, 1.2 ml of triethylamine and 60 ml of dichloromethane. After returning to room temperature, the reaction mixture is washed with 0.1N hydrochloric acid and then with a saturated sodium hydrogen carbonate solution, dried and then evaporated. The resulting residue is dissolved in 20 ml of tetrahydrofuran. The solution is added to a mixture of 1.3 g of AlLiH4 in 60 ml of tetrahydrofuran. The reaction mixture is refluxed for 3 hours and then hydrolysed with 0.65 ml of water, 0.45 ml of 20% sodium hydroxide solution and 2.1 ml of water. After filtration and concentration, the residue is purified by chromatography over silica gel (dichloromethane/ethanol/NH4OH: 95/5/0.5) and recrystallised from isopropyl ether to yield the expected product.

Workup

  1. customAfter returning to room temperature
  2. washthe reaction mixture is washed with 0.1N hydrochloric acid
  3. dry with materialwith a saturated sodium hydrogen carbonate solution, dried
  4. customevaporated
  5. dissolutionThe resulting residue is dissolved in 20 ml of tetrahydrofuran
  6. additionThe solution is added to a mixture of 1.3 g of AlLiH4 in 60 ml of tetrahydrofuran
  7. temperatureThe reaction mixture is refluxed for 3 hours
  8. filtrationAfter filtration and concentration
  9. customthe residue is purified by chromatography over silica gel (dichloromethane/ethanol/NH4OH: 95/5/0.5)
  10. customrecrystallised from isopropyl ether

Sources & evidence

ORD record
ord-e4a996bff7ec4eb28f437118421ac7d7
Source dataset
uspto-grants-2002_07
Patent number
US06420413B2

Reaction notes

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