Sodium Azide → HCID 178476366, compound

HRID 417802Notes

Reaction equation

HRID 417802 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:8][C@H:7](Br)[C@@H:6]1[NH:21][C:22](=[C:24]1[C:29](=[O:30])[CH2:28][C:27]([CH3:32])([CH3:31])[CH2:26][C:25]1=[O:33])[CH3:23])(=[O:3])[CH3:2].C(=O)([O-])O.[Na+].[N-:39]=[N+:40]=[N-:41].[Na+]>C(OCC)(=O)C.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[N:39]([C@H:7]1[O:8][C@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:5]([O:4][C:1](=[O:3])[CH3:2])[C@H:6]1[NH:21][C:22](=[C:24]1[C:29](=[O:30])[CH2:28][C:27]([CH3:32])([CH3:31])[CH2:26][C:25]1=[O:33])[CH3:23])=[N+:40]=[N-:41]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 178476345HCID 178476345, compound

Product 1

HCID 178476366HCID 178476366, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3,6-tri-O-Acetyl-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-α-D-glucopyranosyl bromide (3) (150 g, 0.282 mol) is suspended in ethyl acetate (3 L) and a solution of 10% aqueous sodium hydrogen carbonate (1500 mL) containing sodium azide (22 g, 0.338 mol) is added. Tetrabutylammonium hydrogen sulfate (28.7 g, 30 mol %) was added and the biphasic mixture stirred vigorously for 16 h. The organic layer was then separated, extracted and dried, then the solvent removed at reduced pressure. The residue was chromatographed as above to yield the desired product (105 g, 75%). 1H NMR (500 MHz, CDCl3) δ 13.90 (d, J=9.6, 1H), 5.22 (t, J=9.6, 1H), 5.11 (t, J=9.7, 1H), 4.90 (d, J=8.9, 1H), 4.36 (dd, J=4.5, 12.5, 1H), 4.17 (dd, J=12.4, 1.7, 1H), 3.81-3.91 (m, 2H), 2.60 (s, 3H), 2.42 (s, 2H), 2.36 (s, 2H), 2.11, (s, 3H), 2.04 (s, 3H), 1.03 (s, 3H) M/z 495 (M+H).

Workup

  1. additionis added
  2. customThe organic layer was then separated
  3. extractionextracted
  4. customdried
  5. customthe solvent removed at reduced pressure
  6. customThe residue was chromatographed as above

Sources & evidence

ORD record
ord-d01d32e406c749f9b66f28167fc8c148
Source dataset
uspto-grants-2012_01
Patent number
US08093227B2

Reaction notes

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