Acetic Anhydride → HCID 131730017, compound

HRID 2065445Notes

Reaction equation

HRID 2065445 reaction equation
[N:1]([C@@H:4]1[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([OH:25])[C@@H:14]([CH2:26][N:27]2[C:31](=[O:32])[C:30]3=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]3[C:28]2=[O:37])[O:13][C@H:5]1[S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:2]=[N-:3].[C:38](OC(=O)C)(=[O:40])[CH3:39]>N1C=CC=CC=1>[C:38]([C@@:15]1([OH:25])[C@@H:14]([CH2:26][N:27]2[C:31](=[O:32])[C:30]3=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]3[C:28]2=[O:37])[O:13][C@@H:5]([S:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C@H:4]([N:1]=[N+:2]=[N-:3])[C@H:16]1[O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:40])[CH3:39]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 131730018HCID 131730018, compound

Product 1

HCID 131730017HCID 131730017, compoundYield 597.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under an argon atmosphere, 19 (5.28 g, 10.2 mmol) was dissolved in pyridine (100 ml), and the solution was added with acetic anhydride (1.5 ml, 1.59 mmol, 1.56 equiv) with stirring. After three days, stirring was terminated, and the solvent was evaporated. The residue was dissolved in chloroform, and the solution was washed three times with saturated aqueous sodium hydrogencarbonate in a separating funnel. The organic layer was dried over anhydrous sodium sulfate, then recrystallization was performed by using ethanol (50 ml), and primary crystals were collected to obtain 20 as colorless solid (5.29 g, 9.5 mmol, 93%).

Workup

  1. stirringstirring
  2. customwas terminated
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in chloroform
  5. washthe solution was washed three times with saturated aqueous sodium hydrogencarbonate in a separating funnel
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customrecrystallization
  8. customwere collected

Sources & evidence

ORD record
ord-6624b220c3fe42938b1a1e4a7571cfa7
Source dataset
uspto-grants-2012_10
Patent number
US08288527B2

Reaction notes

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