Diethyl Ether → HCID 49848360, compound

HRID 1619448Notes

Reaction equation

HRID 1619448 reaction equation
[CH3:1][C:2]1[C:3]([O:22][CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][CH2:32][CH:33]([CH3:35])[CH3:34])=[O:30])[CH2:25][CH2:24]2)=[N:4][CH:5]=[N:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][O:19][S:18](=[O:21])[O:17][CH2:16]2)=[CH:11][CH:10]=1.C([O:38]CC)C>C(#N)C.O>[O:21]=[S:18]1(=[O:38])[O:19][CH2:20][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][C:7]3[N:6]=[CH:5][N:4]=[C:3]([O:22][CH:23]4[CH2:24][CH2:25][N:26]([C:29]([O:31][CH2:32][CH:33]([CH3:35])[CH3:34])=[O:30])[CH2:27][CH2:28]4)[C:2]=3[CH3:1])=[CH:10][CH:11]=2)[CH2:16][O:17]1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 49847606HCID 49847606, compound

Product 1

HCID 49848360HCID 49848360, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of iso-butyl 4-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate (100 mg, 0.000198 mole) in acetonitrile (1.2 mL) were added NaIO4 (59 mg, 0.000277 mole) and RuCl3.3H2O (0.5 mg, 0.0000198 mole) in 0.2 mL water. After stirring the suspension at 30° C. for 30 minutes, 0.8 mL water and 1.2 mL diethyl ether were added. The layers were separated, and the aqueous layer was extracted with diethyl ether. The combined ether layer was dried over sodium sulfate, the solvents were evaporated to yield 50 mg product as white solid.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with diethyl ether
  3. dry with materialThe combined ether layer was dried over sodium sulfate
  4. customthe solvents were evaporated

Sources & evidence

ORD record
ord-a3fa94e9d3c14a84a57bc0167c4c6747
Source dataset
uspto-grants-2014_07
Patent number
US08772302B2

Reaction notes

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