Methyl N-(triethylammoniosulfonyl)carbamate → 2-(6-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazin-3-yl)-5-methyloxazole

HRID 46201Notes

Reaction equation

HRID 46201 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([C@H:22]2[C@H:27]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C@@H:26]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C@H:25]([O:44][CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C@@H:24]([CH2:52][O:53][CH2:54][C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[O:23]2)=[CH:18][C:3]=1[CH2:4][C:5]1[N:10]=[N:9][C:8]([C:11]([NH:13][CH2:14][C:15](=O)[CH3:16])=[O:12])=[CH:7][CH:6]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([C@H:22]2[C@H:27]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C@@H:26]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C@H:25]([O:44][CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C@@H:24]([CH2:52][O:53][CH2:54][C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)[O:23]2)=[CH:18][C:3]=1[CH2:4][C:5]1[N:10]=[N:9][C:8]([C:11]2[O:12][C:15]([CH3:16])=[CH:14][N:13]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 672883166-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-N-(2-oxopropyl)pyridazine-3-carboxamide

Product 1

HCID 672873392-(6-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazin-3-yl)-5-methyloxazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-N-(2-oxopropyl)pyridazine-3-carboxamide (1.2 mmol) form Step 1 in tetrahydrofuran (30 mL) was added Burgess reagent (343 mg, 1.4 mmol). The reaction mixture was refluxed overnight. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered through a plug of silica gel and concentrated in vacuo. The resulting crude residue was used without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered through a plug of silica gel
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude residue was used without further purification

Sources & evidence

ORD record
ord-9230953c13cd4a4296d1d5676b436bc6
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

Loading…