Sodium Azide → HCID 178476366, compound

HRID 2220494Notes

Reaction equation

HRID 2220494 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

3,4,6-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 mnL) containing sodium azide (22 g, 0.338 mol) is added. Tetrabutylammonium hydrogen sulfate (28.7 g, 30 mol %) was added and the biphasic mnixture 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-49774868ff294f679cb3a664549820c9
Source dataset
uspto-grants-2008_08
Patent number
US07417129B2

Reaction notes

Loading…