Benzylamine → HCID 86659941, compound

HRID 400335Notes

Reaction equation

HRID 400335 reaction equation
C([O:4][C@H:5]1[O:22][C@H:21]([CH2:23][N:24]=[N+:25]=[N-:26])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.C(N)C1C=CC=CC=1>C1COCC1>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:21]([CH2:23][N:24]=[N+:25]=[N-:26])[O:22][C@@H:5]1[OH:4])(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 12127419HCID 12127419, compound

Product 1

HCID 86659941HCID 86659941, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,2,3,4-tetra-O-acetyl-6-azido-6-deoxy-α-D-glucopyranose (IV, 850 mg, 2.78 mmol) in THF (12 mL) was added benzylamine (0.23 mL) and the mixture was stirred at rt overnight. Solvents were removed under the reduced pressure and the resulting residue was dissolved in dichloromethane (50 mL) and washed with water, saturated ammonia chloride, brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography, eluting with 1:1 hexane-ethyl acetate, to give V (640 mg, 85%) as a white foam. 1H NMR (500.1 MHz) (CD3Cl) δ: 5.50 (m, 2H), 5.03 (t, J=10.5 Hz, 1H), 4.90 (m, 1H), 4.24 (m, 1H), 3.35 (m, 2H), 2.12 (s, 3H), 2.05 (s, 3H), 2.02 (s, 3H). 13C NMR (125.8 MHz) (CDCl3) δ: 170.26, 170.23, 169.78, 89.98, 71.09, 69.71, 68.34, 51.05, 20.68, 20.62, 20.58.

Workup

  1. customSolvents were removed under the reduced pressure
  2. dissolutionthe resulting residue was dissolved in dichloromethane (50 mL)
  3. washwashed with water, saturated ammonia chloride, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 1:1 hexane-ethyl acetate
  8. customto give V (640 mg, 85%) as a white foam

Sources & evidence

ORD record
ord-af73a0d77efb4ca3aeadec24f017d7c2
Source dataset
uspto-grants-2014_06
Patent number
US08741567B2

Reaction notes

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