Triethylamine → HCID 18956267, compound

HRID 1656016Notes

Reaction equation

HRID 1656016 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:16][N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)([CH2:12][CH2:13][CH2:14][CH3:15])C(O)=O)=[CH:4][CH:3]=1.C1(P([N:36]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>C(O)(C)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH2:36])([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:16][N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 15766659HCID 15766659, compound

Product 1

HCID 18956267HCID 18956267, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a stirred solution of 1.0 g (3.25 mmols) of 2-(4-chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanoic acid in 10 mL of tert-butanol was added 0.87 mL (3.25 mmols) of diphenylphosphorylazide followed by 0.33 mL of triethylamine. This mixture was heated to relux for 48 hours. The tert-butanol was removed under reduced pressure and the residue was taken up in 5% hydrochloric acid and washed with ethyl acetate. The acidic aqueous layer was made basic with concentrated ammonium hydroxide and extracted with ethyl acetate. Removal of solvents from the organic extract afforded 0.510 g (57%) of the amine as a viscous oil: 1H-NMR (CDCl3, Me4Si) 0.8-1.2 (t,J=6 Hz, CH2 --CH3), 1.2-1.7 (m), 1.7-2.2 (m), 2.0 (br s, --NH2), 4.6 (s, CH2 --N), 7.45 (s, phenyl H), 7.8 (s, CH=N), 8.0 ppm (s, CH=N);

Workup

  1. temperatureThis mixture was heated
  2. customThe tert-butanol was removed under reduced pressure
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. customRemoval of solvents from the
  6. extractionorganic extract

Sources & evidence

ORD record
ord-ae22a3d4dc1545588f6a5e65c66f5d24
Source dataset
uspto-grants-1993_10
Patent number
US05252594

Reaction notes

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