Diethyl Ether → HCID 86664430, compound

HRID 46214Notes

Reaction equation

HRID 46214 reaction equation
ClC1[CH:15]=[CH:14][C:13]([C@H:16]2[C@H:21]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:20]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@H:19]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@@H:18]([CH2:46][O:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[O:17]2)=[CH:12][C:3]=1[CH2:4][C:5]1[NH:10][CH2:9][C:8](=O)[NH:7][N:6]=1.C(C1C(=O)C([Cl:65])=C(Cl)C(=O)C=1C#N)#N.CCOCC.[CH2:74]([Cl:76])Cl>O>[Cl:65][C:8]1[N:7]=[N:6][C:5]([CH2:4][C:3]2[CH:12]=[C:13]([C@H:16]3[C@H:21]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C@@H:20]([O:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C@H:19]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C@@H:18]([CH2:46][O:47][CH2:48][C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[O:17]3)[CH:14]=[CH:15][C:74]=2[Cl:76])=[N:10][CH:9]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 178516766HCID 178516766, compound2×

Product 1

HCID 86664430HCID 86664430, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

The 3-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)-4,5-dihydro-1,2,4-triazin-6(1H)-one (compound 55, 826 mg, 1.11 mmol) in a mixture of CH2Cl2 (20 ml) and water (2 ml) treated with DDQ (504 mg, 2.22 mmol) at 0° C. After 3 hours, Et2O and water were added to the reaction mixture. Normal work-up with CH2Cl2 and drying with MgSO4 generated crude title compound. Without further purification, it was reacted with POCl3 (2 ml) in toluene (20 ml) under refluxed condition. After reaction complete, the resulting solution was poured into iced water (50 ml). After work-up with CH2Cl2, organic layer was evaporated under reduced pressure. The residue was purified with use of column chromatography (Hexane/EtOAc=½) to provide title compound (296 mg, 35% overall yield) as yellow oil.

Workup

  1. dry with materialNormal work-up with CH2Cl2 and drying with MgSO4
  2. customWithout further purification, it
  3. customwas reacted with POCl3 (2 ml) in toluene (20 ml)
  4. temperatureunder refluxed condition
  5. customAfter reaction complete
  6. customAfter work-up with CH2Cl2, organic layer was evaporated under reduced pressure
  7. customThe residue was purified with use of column chromatography (Hexane/EtOAc=½)

Sources & evidence

ORD record
ord-bb6fc52594da4d918ee845eb49d68ebe
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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