Ethyl Acetate → Methyl 2-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)-2-(7-methylbenzo[e][1,2,4]triazin-3-yl)acetate

HRID 46209Notes

Reaction equation

HRID 46209 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9]2)=[CH:4][C:3]=1[CH:47]([C:52]1[N:53]=[N+:54]([O-])[C:55]2[CH:61]=[C:60]([CH3:62])[CH:59]=[CH:58][C:56]=2[N:57]=1)[C:48]([O:50][CH3:51])=[O:49].[Cl-].[NH4+].CCOC(C)=O>O1CCOCC1.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[O:9]2)=[CH:4][C:3]=1[CH:47]([C:52]1[N:53]=[N:54][C:55]2[CH:61]=[C:60]([CH3:62])[CH:59]=[CH:58][C:56]=2[N:57]=1)[C:48]([O:50][CH3:51])=[O:49]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 672874843-(1-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)-2-methoxy-2-oxoethyl)-7-methylbenzo[e][1,2,4]triazine 1-oxide2×

Product 1

HCID 67287553Methyl 2-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)-2-(7-methylbenzo[e][1,2,4]triazin-3-yl)acetateYield 75%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 312751,4-DioxaneSolvent

Procedure

3-(1-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)-2-methoxy-2-oxoethyl)-7-methylbenzo[e][1,2,4]triazine 1-oxide (compound 61, 310 mg, 0.36 mmol) was treated with Zn (500 mg, 7.6 mmol) and ammonium chloride (500 mg, 9.34 mmol) in aqueous dioxane at room temperature for 1 day. The reaction mixture was diluted and work-up with EtOAc. After evaporating the volatile solvent under reduced pressure, the residue was purified with silica gel column (Hx/EtOAc=⅓) to afford title compound (228 mg, 75% yield) as white solid.

Workup

  1. additionThe reaction mixture was diluted
  2. customAfter evaporating the volatile solvent under reduced pressure
  3. customthe residue was purified with silica gel column (Hx/EtOAc=⅓)

Sources & evidence

ORD record
ord-5a50017941954f0ebb346b154195d7f1
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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