Acetone → HCID 491151, compound

HRID 1280093Notes

Reaction equation

HRID 1280093 reaction equation
[CH3:1][O:2][C:3](=[O:40])[C@@H:4]([NH:17][C:18]([C:20]1[CH:39]=[CH:38][C:23]2[N:24]([CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[C:25]([C:27]3[CH:31]=[CH:30][O:29][CH:28]=3)=[N:26][C:22]=2[CH:21]=1)=[O:19])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[N:8]([CH3:16])[CH:7]=1.[C:41](=[O:44])([O-])[O-:42].[Cs+].[Cs+].[CH3:47][C:48]([CH3:50])=O>O>[CH3:1][O:2][C:3](=[O:40])[C@@H:4]([NH:17][C:18]([C:20]1[CH:39]=[CH:38][C:23]2[N:24]([CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)[C:25]([C:27]3[CH:31]=[CH:30][O:29][CH:28]=3)=[N:26][C:22]=2[CH:21]=1)=[O:19])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:48]([C:41]([OH:42])=[O:44])([CH3:50])[CH3:47])[CH:13]=2)[N:8]([CH3:16])[CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 10796Cesium carbonateHCID 491150HCID 491150, compound

Product 1

HCID 491151HCID 491151, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The title compound of example 114 (0.097 g, 0.18 mmol) was dissolved in acetone (1.5 mL). Cesium carbonate (0.175 g, 0.54 mmol) and teft-butylbromoisobutyrate (0.080 g, 0.36 mmol) were added and the mixture stirred at 60° C. overnight in a sealed tube. The reaction mixture was then diluted with water (10 mL) and the product extracted with EtOAc (50 mL). The organic phase was dried (MgSO4), concentrated and the residue purified by flash chromatography using 60-80% EtOAc in hexane as eluent. The purified diester was dissolved in DCM (0.5 mL) and TFA (0.5 mL) was added. After stirring at room temperature for 1.5 h, volatiles were removed under a stream of nitrogen and the residue purified by preparative C18 reversed-phase HPLC to give the title compound of example 115.

Workup

  1. extractionthe product extracted with EtOAc (50 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated
  4. customthe residue purified by flash chromatography
  5. dissolutionThe purified diester was dissolved in DCM (0.5 mL)
  6. additionTFA (0.5 mL) was added
  7. stirringAfter stirring at room temperature for 1.5 h
  8. customvolatiles were removed under a stream of nitrogen
  9. customthe residue purified by preparative C18 reversed-phase HPLC

Sources & evidence

ORD record
ord-4659ebc2d9224dc3b16a5d9d3f25dcda
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

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