Acetyl chloride → HCID 21187761, compound

HRID 1383467Notes

Reaction equation

HRID 1383467 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][OH:7].[F:8][C:9]([F:16])([F:15])[C:10](OCC)=[O:11].C(N(CC)CC)C.[C:24](Cl)(=[O:26])[CH3:25]>CO>[C:24]([N:4]([CH2:5][CH2:6][OH:7])[CH2:3][CH2:2][NH:1][C:10](=[O:11])[C:9]([F:16])([F:15])[F:8])(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 8471TriethylamineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 21187761HCID 21187761, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(2-aminoethylamino)ethanol (1.15 g, 11 mmol, 1.10 equiv) in 50 mL MeOH at 0° C. was slowly added ethyl trifluoroacetate (1.42 g, 10 mmol, 1.00 equiv). The mixture was stirred at room temperature for 5 hours. Solvents were then removed, and the residue was dissolved in 50 mL methylene chloride. Triethylamine (1.52 g, 15 mmol) was added followed by acetyl chloride (0.94 g, 12 mmol, 1.20 equiv). Removal of solvent yielded N-acetyl-N-(2-trifluoroacetylaminoethyl)-(2′-hydroxyethyl)amine (crude) as a white solid. This crude product was subjected to a series of reactions similar to those for SBR-11-4416. 0.60 g final product was isolated as a white solid after HPLC purification. 1H NMR (CDCl3, ppm): 8.47(d, 2H), 7.99 (brs, 2H), 7.14-7.35 (m, 10H), 5.20 (s, 1H), 2.96-3.56 (m, 12H), 2.18 (s, 3H). MS: 482.24 (calc'd); 483.5 (M+1).

Workup

  1. customat 0° C.
  2. customSolvents were then removed
  3. dissolutionthe residue was dissolved in 50 mL methylene chloride
  4. customRemoval of solvent

Sources & evidence

ORD record
ord-09f4d77f5e584876b25e64b7089ca5a0
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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