Triethylamine → HCID 15680031, compound

HRID 1494194Notes

Reaction equation

HRID 1494194 reaction equation
[C:1]([OH:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:8]([OH:14])(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].[NH2:15][CH2:16][CH2:17][C:18]1[CH:25]=[CH:24][C:22](O)=[C:20](O)[CH:19]=1.C(N(CC)CC)C.Cl[C:34]([O:36][CH2:37][Cl:38])=[O:35]>O1CCCC1>[C:1]([O:7][C:20]1[CH:19]=[C:18]([CH2:17][CH2:16][NH:15][C:34]([O:36][CH2:37][Cl:38])=[O:35])[CH:25]=[CH:24][C:22]=1[O:13][C:8](=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 62754Chloromethyl chloroformateHCID 131716755HCID 131716755, compound

Product 1

HCID 15680031HCID 15680031, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dopamine dipivalate, oxalate salt (822 mg, 2 mmol) was suspended in 15 mL of dry tetrahydrofuran. Triethylamine (278 mL, 1 mmol) was added, the mixture was stirred for 15 minutes and a further 278 mL (1 mmol) of triethylamine were then added. Addition of ClCO2CH2Cl (390 mg, 6 mmol) resulted in immediate formation of a heavy white precipitate and the evolution of gas. The reaction mixture was stirred overnight at room temperature, then the precipitate was removed by filtration and the filtrate was washed with 10 mL of 0.1M hydrochloric acid. Drying over magnesium sulfate and evaporation to dryness afforded 1.1 g of a golden oil of the structural formula ##STR140## The identity of the product was confirmed by elemental analysis.

Workup

  1. customresulted in immediate formation of a heavy white precipitate
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. customthe precipitate was removed by filtration
  4. washthe filtrate was washed with 10 mL of 0.1M hydrochloric acid
  5. dry with materialDrying over magnesium sulfate and evaporation to dryness

Sources & evidence

ORD record
ord-78e1f207e5904612ae2eae475bd400bf
Source dataset
uspto-grants-1991_06
Patent number
US05024998

Reaction notes

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