Acetic Anhydride → HCID 90060443, compound

HRID 1779257Notes

Reaction equation

HRID 1779257 reaction equation
[OH:1][C@@:2]([CH2:46][CH2:47][OH:48])([C@@H:10]([C:28](=[O:45])[NH:29][C@H:30]([C:39]1[O:40][C:41]([CH3:44])=[CH:42][N:43]=1)[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1)/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:56][C:57]#[C:58][CH3:59].[C:60](OC(=O)C)(=[O:62])[CH3:61].C(N(CC)CC)C>CN(C=O)C.[Cl-].[Na+].O.CN(C1C=CN=CC=1)C>[C:60]([O:48][CH2:47][CH2:46][C@:2]([OH:1])([C@@H:10]([C:28](=[O:45])[NH:29][C@H:30]([C:39]1[O:40][C:41]([CH3:44])=[CH:42][N:43]=1)[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([O:38][CH2:56][C:57]#[C:58][CH3:59])=[CH:36][CH:37]=1)/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])(=[O:62])[CH3:61]

Participants

9

Reactant 5

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 90060269HCID 90060269, compound

Product 1

HCID 90060443HCID 90060443, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent2×

Procedure

tert-Butyl (E)-(2S,3S)-2-hydroxy-2-(2-hydroxy-ethyl)-3-[(S)-2-(4-hydroxy-phenyl)-1-(5-methyl-oxazol-2-yl)-ethylcarbamoyl]-12-oxo-nonadec-4-enoate (3.5 mg, 5.22 μmol) was dissolved in DMF (0.3 mL), and potassium carbonate (1.4 mg, 10.4 μmol) and 1-bromo-but-2-yne (0.7 μL, 7.83 μmol) were added. The mixture was stirred at room temperature for 24 hours. A saturated brine was then added to the reaction mixture, which was followed by extraction with ethyl acetate. The organic extract was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane (0.5 mL), and acetic anhydride (1.0 μL, 10.4 μmol), DMAP (0.06 mg, 0.52 μmol), and triethylamine (2.9 μL, 20.9 μmol) were added. The mixture was stirred at room temperature for 9 hours. A saturated brine was then added to the reaction mixture, which was followed by extraction with ethyl acetate. The organic extract was dried over magnesium sulfate, and concentrated under reduced pressure to obtain the title compound (4 mg).

Workup

  1. extractionwas followed by extraction with ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in dichloromethane (0.5 mL)
  6. stirringThe mixture was stirred at room temperature for 9 hours
  7. extractionwas followed by extraction with ethyl acetate
  8. extractionThe organic extract
  9. dry with materialwas dried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b48447e072d9402698687add4b7d3908
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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