Pyridine → (2R)-2-({Formyl[(phenylmethyl)oxy]amino}methyl)hexanoyl fluoride

HRID 1396864Notes

Reaction equation

HRID 1396864 reaction equation
[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:17][CH2:18][CH2:19][CH3:20])[C:14](O)=[O:15])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:2].N1C=CC=CC=1.[F:27]C1N=C(F)N=C(F)N=1>C(Cl)Cl>[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]([F:27])=[O:15])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 11185069(2R)-2-({Formyl[(phenylmethyl)oxy]amino}methyl)hexanoic acid

Product 1

HCID 86706342(2R)-2-({Formyl[(phenylmethyl)oxy]amino}methyl)hexanoyl fluorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)hexanoic acid (9) (1.7 g, 6.1 mmol) in DCM (20 mL) was added pyridine (0.53 g, 6.7 mmol), followed by 2,4,6-trifluoro-1,3,5-triazine (0.86 g, 6.4 mmol) dropwise. The reaction mixture was stirred for 4 h and TLC indicated completion of the reaction. The reaction mixture was washed with 10% aqueous citric acid and brine, dried over Na2SO4, and concentrated to provide the title compound (1.7 g, 100%) as red oil. 1H NMR (300 MHz, DMSO) δ ppm 0.86 (t, J=6.7 Hz, 3H), 1.16-1.38 (m, 4H), 1.57 (m, 2H), 3.03 (m, 1H), 3.87 (m, 2H), 4.91 (s, 2H), 7.41 (m, 5H).

Workup

  1. customcompletion of the reaction
  2. washThe reaction mixture was washed with 10% aqueous citric acid and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-13737076165644e5a45aac3e696ee427
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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