Ethanolamine → HCID 19600242, compound

HRID 611257Notes

Reaction equation

HRID 611257 reaction equation
[C:1]([C:9]1[CH:28]=[CH:27][C:12]([C:13]([N:15]2[CH2:20][CH2:19][C:18]3[CH:21]=[C:22]([C:24](O)=[O:25])[O:23][C:17]=3[CH2:16]2)=[O:14])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:29][CH2:30][CH2:31][OH:32].C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>C(#N)C>[OH:32][CH2:31][CH2:30][NH:29][C:24]([C:22]1[O:23][C:17]2[CH2:16][N:15]([C:13](=[O:14])[C:12]3[CH:27]=[CH:28][C:9]([C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:10][CH:11]=3)[CH2:20][CH2:19][C:18]=2[CH:21]=1)=[O:25]

Participants

8

Reactant 6

HCID 700EthanolamineHCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 19600266HCID 19600266, compound

Product 1

HCID 19600242HCID 19600242, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.545 g (1.452 mmol) of 6-(4-benzoylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine-2-carboxylic acid, 98 mg (1.6 mmol) of 2-aminoethanol, 0.61 ml (4.4 mmol) of triethylamine and 1.40 ml (14.5 mmol) of carbon tetrachloride in 20 ml of acetonitrile, 1.14 g (4.36 mmol) of triphenylphosphine was added under ice-cooling, followed by stirring at room temperature for 4 hours. The reaction mixture was poured into aqueous sodium hydroxide and extracted with ethyl acetate 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 (ethyl acetate to ethyl acetate/methanol=9/1); the resulting solid was washed with diethyl ether to yield the desired product.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate 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 (ethyl acetate to ethyl acetate/methanol=9/1)
  6. washthe resulting solid was washed with diethyl ether

Sources & evidence

ORD record
ord-0fde3147b70742288e94cc35008d1e5d
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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