Triethylamine → HCID 19599881, compound

HRID 611222Notes

Reaction equation

HRID 611222 reaction equation
Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3]1.[C:12]([C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[OH-].[Na+]>ClCCl>[C:12]([C:20]1[CH:21]=[CH:22][C:23]([C:24]([N:8]2[CH2:9][CH2:10][CH2:11][C:5]3[CH:4]=[CH:3][O:2][C:6]=3[CH2:7]2)=[O:25])=[CH:27][CH:28]=1)(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 691474-Benzoylbenzoic acidHCID 76257Diethyl cyanophosphonateHCID 19599956HCID 19599956, compound

Product 1

HCID 19599881HCID 19599881, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.128 g of the above crude 5,6,7,8-tetrahydro-4H-furo[2,3-c]azepine hydrochloride, 0.21 g (0.94 mmol) of 4-benzoylbenzoic acid and 0.43 ml (3.1 mmol) of triethylamine in 30 ml of dichloromethane, 0.14 ml (0.94 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 1/1) 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 1/1)

Sources & evidence

ORD record
ord-47e0a82e926e4d25a1e7b625c3d8e2c0
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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