Triethylamine → HCID 66685338, compound

HRID 922333Notes

Reaction equation

HRID 922333 reaction equation
[C:1]([O:9][C:10]1[CH:28]=[CH:27][C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](O)=[O:25])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:30](OCC)=O.C(N(CC)CC)C.[NH4+:42].[OH-:43]>C1COCC1>[O:43]=[C:2]([C:3]1[CH:30]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:1][O:9][C:10]1[CH:28]=[CH:27][C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([NH2:42])=[O:25])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 86695807HCID 86695807, compound

Product 1

HCID 66685338HCID 66685338, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 100 mL RB flask fitted with magnetic stirrer was charged 12 mL THF to the stirred solvent was added 3-(4-{[4-(benzoyloxy)benzyl]oxy}phenyl)propanoic acid (1 g, 2.4 mmol), Ethyl chloroformate (0.36 mL, 38 mmol) and Tri ethyl amine (1.4 mL, 10 mmol) was added −10° C. Then it was stirred at same temp. 45 min then added NH4OH, continued the stirring at same temperature for 1 h. After completion of the reaction (reaction monitored by TLC), reaction mass was extracted with ethyl acetate and water. The organic layer washed with brine and dried by Na2SO4 and evaporated to dryness to get the compound (1 g, Yield: 99%). MS (ESI, 120 eV): m/z=390.2 (M−H)+.

Workup

  1. customTo a 100 mL RB flask fitted with magnetic stirrer
  2. additionwas added −10° C
  3. custom45 min
  4. customfor 1 h
  5. customAfter completion of the reaction (reaction monitored by TLC), reaction mass
  6. extractionwas extracted with ethyl acetate and water
  7. washThe organic layer washed with brine
  8. dry with materialdried by Na2SO4
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-4e86e0d2b30f459099817cfc79fc2742
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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