Diethylamine → HCID 86589128, compound

HRID 1821453Notes

Reaction equation

HRID 1821453 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16]([CH2:18][CH2:19][C@@H:20]([NH:28]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:17])=[N+:2]=[N-:3].C(NCC)C>C(Cl)Cl>[NH2:28][C@H:20]([CH2:19][CH2:18][C:16](=[O:17])[NH:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])[C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86589129HCID 86589129, compound

Product 1

HCID 86589128HCID 86589128, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 103 (2.7 g, 4.3 mmol) was dissolved in 30 ml methylene chloride and 30 ml diethylamine was added. The reaction mixture was stirred at room temperature for 2 h, and then concentrated to an oil under reduced pressure. The residue was dissolved with diethyl ether and ethyl acetate (ca. 50 ml ea.) and extracted with 10% citric acid. The aqueous layer was neutralized to pH13 with 10N NaOH and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give 1.6 g of a brown oil, 4.0 mmol, 92% (compound 104).

Workup

  1. concentrationconcentrated to an oil under reduced pressure
  2. dissolutionThe residue was dissolved with diethyl ether and ethyl acetate (ca. 50 ml ea.)
  3. extractionextracted with 10% citric acid
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ffbc9036930b4014a8a0f60cad657368
Source dataset
uspto-grants-2009_10
Patent number
US07605175B2

Reaction notes

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