Triethylamine → HCID 19600220, compound

HRID 611243Notes

Reaction equation

HRID 611243 reaction equation
[O:1]1[C:5]2[CH2:6][NH:7][CH2:8][CH2:9][C:4]=2[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11].[C:14]1([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](O)=[O:26])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[OH-].[Na+]>ClCCl>[C:14]1([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([N:7]2[CH2:8][CH2:9][C:4]3[CH:3]=[C:2]([C:10]([O:12][CH3:13])=[O:11])[O:1][C:5]=3[CH2:6]2)=[O:26])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 76257Diethyl cyanophosphonateHCID 796956-Phenylhexanoic AcidHCID 19600098Methyl 4,5,6,7-tetrahydrofuro[2,3-c]pyridine-2-carboxylate

Product 1

HCID 19600220HCID 19600220, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 95 mg (0.52 mmol) of methyl 4,5,6,7-tetrahydrofuro[2,3-c]pyridine-2-carboxylate, 0.12 g (0.63 mmol) of 6-phenylhexanoic acid and 0.15 ml (1.0 mmol) of triethylamine in 30 ml of dichloromethane, 0.10 ml (0.63 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. The reaction mixture was poured into aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 2/1) to yield the desired product.

Workup

  1. temperaturecooling
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 2/1)

Sources & evidence

ORD record
ord-5b76d495b2bd41ba8f74873a006985ce
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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