Cesium carbonate → Methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-{2-[2-(2-oxo-1,3-oxazolidin-3-yl)ethoxy]-phenyl}pent-4-en-1-yl]benzoate

HRID 1512220Notes

Reaction equation

HRID 1512220 reaction equation
CC1C=CC(S([O:11][CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][O:16][C:15]2=[O:19])(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].O[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1/[CH:33]=[CH:34]/[CH:35]([CH2:48][C:49]1[CH:54]=[CH:53][C:52]([C:55]([O:57][CH3:58])=[O:56])=[CH:51][CH:50]=1)[CH2:36][CH2:37][C:38]1[CH:47]=[CH:46][C:41]([C:42]([O:44][CH3:45])=[O:43])=[CH:40][CH:39]=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH3:58][O:57][C:55]([C:52]1[CH:51]=[CH:50][C:49]([CH2:48][CH:35](/[CH:34]=[CH:33]/[C:28]2[CH:27]=[CH:32][CH:31]=[CH:30][C:29]=2[O:11][CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][O:16][C:15]2=[O:19])[CH2:36][CH2:37][C:38]2[CH:47]=[CH:46][C:41]([C:42]([O:44][CH3:45])=[O:43])=[CH:40][CH:39]=2)=[CH:54][CH:53]=1)=[O:56]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 157609472-(2-Oxooxazolidin-3-yl)ethyl 4-methylbenzenesulfonateHCID 59437428Methyl 4-{(4E)-5-(2-hydroxyphenyl)-3-[4-(methoxycarbonyl)benzyl]pent-4-en-1-yl}benzoate

Product 1

HCID 59437419Methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-{2-[2-(2-oxo-1,3-oxazolidin-3-yl)ethoxy]-phenyl}pent-4-en-1-yl]benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 82.0 mg (0.288 mmol) of 2-(2-oxo-1,3-oxazolidin-3-yl)ethyl 4-methylbenzenesulfonate [CAS Reg. No. 159974-55-7] is initially charged in 1.5 ml of dry toluene, and 187 mg (0.576 mmol) of cesium carbonate are added. 32 mg (0.072 mmol) of methyl 4-{(4E)-5-(2-hydroxy-phenyl)-3-[4-(methoxycarbonyl)benzyl]pent-4-en-1-yl}benzoate (racemate; Example 18A) are then added. The reaction mixture is stirred at 60° C. for 18 h and then carefully poured into 15 ml of ice-cold 10% strength ammonium chloride solution. The mixture is extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and concentrated. This gives 39 mg (0.070 mmol, 97% of theory) of a colorless oil which is reacted without further purification

Workup

  1. extractionThe mixture is extracted twice with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThis gives 39 mg (0.070 mmol, 97% of theory) of a colorless oil which is reacted without further purification

Sources & evidence

ORD record
ord-4bcbc29d849a4f56acc2fde01fafe4c9
Source dataset
uspto-grants-2012_07
Patent number
US08217063B2

Reaction notes

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