4-Fluorobenzylamine → HCID 58929056, compound

HRID 853635Notes

Reaction equation

HRID 853635 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:13][C:14]([OH:16])=O)[CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(C1NC=CN=1)(C1NC=CN=1)=O.[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10](=[O:12])[N:35]([CH2:34][C:33]2[CH:36]=[CH:37][C:30]([F:29])=[CH:31][CH:32]=2)[C:14](=[O:16])[CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 673264-FluorobenzylamineHCID 2755971N-(tert-Butoxycarbonyl)iminodiacetic AcidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 58929056HCID 58929056, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 27 (547 mg, 2.35 mmol) and carbonyl diimidazole (837 mg, 5.16 mmol) in 4.7 mL of dry THF under a N2 atmosphere was refluxed for 5 minutes. Once the reaction cooled down to room temperature 4-fluorobenzyl amine (0.295 mL, 2.58 mmol) was added and the mixture was heated to reflux overnight. The reaction mixture was then concentrated and re-dissolved in EtOAc. The organic layer was washed with an aqueous 0.5 N HCl solution and the solvent was removed in vacuo. The product was purified by column chromatography eluting with CH2Cl2 to provide clean product 28 as a clear oil. 1H NMR (300 MHz, CDCl3) δ 1.47 (s, 9H), 4.39 (s, 4H), 4.92 (s, 2H), 6.99 (t, 2H, J=9 Hz), 7.40 (dd, 2H, J=5, 9 Hz); 13C NMR (75 MHz, CDCl3) δ 28.1, 42.0, 47.1, 82.3, 115.2, 115.5, 131.1, 131.2, 132.0, 153.0, 162.7 (d, J=245 Hz), 168.0; 19F NMR (282.6 MHz, CDCl3) δ 62.5; EI MS (m/z) 340.5 [M+Na].

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux overnight
  4. concentrationThe reaction mixture was then concentrated
  5. dissolutionre-dissolved in EtOAc
  6. washThe organic layer was washed with an aqueous 0.5 N HCl solution
  7. customthe solvent was removed in vacuo
  8. customThe product was purified by column chromatography
  9. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-0fdd06faf4f24967b3a199c4d0a3dc44
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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