Acetic Acid → HCID 12127419, compound

HRID 400334Notes

Reaction equation

HRID 400334 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:11]([O:17][C:18](=[O:20])[CH3:19])[C@@H:10]([CH2:21][N:22]=[N+:23]=[N-:24])[O:9][C@@H:6]1OC)(=[O:3])[CH3:2].S(=O)(=O)(O)O.[C:30]([OH:33])(=[O:32])[CH3:31]>C(OC(=O)C)(=O)C>[C:30]([O:33][C@H:6]1[O:9][C@H:10]([CH2:21][N:22]=[N+:23]=[N-:24])[C@@H:11]([O:17][C:18](=[O:20])[CH3:19])[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:5]1[O:4][C:1](=[O:3])[CH3:2])(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 71662858HCID 71662858, compound

Product 1

HCID 12127419HCID 12127419, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranoside (III, 1.0 g, 2.9 mmol) in acetic acid (20 mL) and acetic anhydride (20 mL) at 0° C. was added sulfuric acid (97%, 1 mL) and the mixture was stirred at rt for 20 hr and then poured into ice (100 g). Extraction with dichloromethane (3×50 mL) and washed with water, saturated sodium bicarbonate, brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography, eluting with 1:1 hexane-ethyl acetate, to give IV (886 mg, 82%) as a white foam. 1H NMR (500.1 MHz) (CD3Cl) δ: 6.28 (d, J=4.0 Hz, 1H), 5.41 (t, J=9.5 Hz, 1H), 5.03 (m, 2H), 4.03 (m, 1H), 3.24-3.37 (m, 2H), 2.13 (s, 3H), 2.04 (s, 3H), 1.99 (s, 3H), 1.95 (s, 3H). 13C NMR (125.8 MHz) (CDCl3) δ: 170.11, 169.53, 169.33, 168.62, 88.78, 70.83, 69.58, 69.08, 68.94, 50.61, 20.75, 20.55, 20.46, 20.34.

Workup

  1. extractionExtraction with dichloromethane (3×50 mL)
  2. washwashed with water, saturated sodium bicarbonate, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 1:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-daf2b49341f7443d894bc00cc574df0c
Source dataset
uspto-grants-2014_06
Patent number
US08741567B2

Reaction notes

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