Cesium carbonate → HCID 491151, compound

HRID 2117016Notes

Reaction equation

HRID 2117016 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(=O)([O-])[O-].[Cs+].[Cs+].C([CH2:51][C:52](Br)([CH3:56])[C:53]([O-:55])=[O:54])(C)(C)C>CC(C)=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:52]([C:53]([OH:55])=[O:54])([CH3:56])[CH3:51])[CH:13]=2)[N:8]([CH3:16])[CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 491150HCID 491150, compoundHCID 53400821HCID 53400821, compound

Product 1

HCID 491151HCID 491151, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 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 tert-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-c4e188ce4a534d499ebcdea3f6bcf489
Source dataset
uspto-grants-2008_10
Patent number
US07439258B2

Reaction notes

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