HCID 24785288, compound → HCID 24785043, compound

HRID 1717508Notes

Reaction equation

HRID 1717508 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:6]([N:8]([CH2:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=2[O:21][CH2:22][CH2:23][O:24]C2CCCCO2)[C:9](=[O:11])[CH3:10])[CH:7]=1>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[C:6]([N:8]([CH2:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=2[O:21][CH2:22][CH2:23][OH:24])[C:9](=[O:11])[CH3:10])[CH:7]=1

Participants

3

Reactant 1

HCID 24785288HCID 24785288, compound

Product 1

HCID 24785043HCID 24785043, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1.53 g (3.0 mmol) 1d in 15 ml methanol was added a catalytic amount of tosyl acid. The reaction mixture was stirred for 4 h at 25° C. The reaction mixture was poured in ice-cold ethyl acetate. The solution was washed twice with ice-cold diluted aqueous sodium hydrogen carbonate solution and brine and dried with magnesium sulfate. The crude product was purified by silica column chromatography (ethyl acetate:hexane gradient 1:4-1:2). The desired product 1e was obtained in 71% yield (0.91 g, 2.13 mmol) as yellow oil.

Workup

  1. additionThe reaction mixture was poured in ice-cold ethyl acetate
  2. washThe solution was washed twice with ice-cold diluted aqueous sodium hydrogen carbonate solution and brine
  3. dry with materialdried with magnesium sulfate
  4. customThe crude product was purified by silica column chromatography (ethyl acetate:hexane gradient 1:4-1:2)

Sources & evidence

ORD record
ord-e2b56067418645da98e14fe8c374dc42
Source dataset
uspto-grants-2010_09
Patent number
US07803960B2

Reaction notes

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