Sodium hydride → Methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-(2-{[5-(2-oxo-1,3-oxazolidin-3-yl)pentyl]oxy}-phenyl)pent-4-en-1-yl]benzoate

HRID 1512216Notes

Reaction equation

HRID 1512216 reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].[H-].[Na+].Cl[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1/[CH:22]=[CH:23]/[CH:24]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]([O:46][CH3:47])=[O:45])=[CH:40][CH:39]=1)[CH2:25][CH2:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=1.[Cl-].[NH4+]>CN(C=O)C>[CH3:47][O:46][C:44]([C:41]1[CH:40]=[CH:39][C:38]([CH2:37][CH:24](/[CH:23]=[CH:22]/[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][N:3]2[CH2:4][CH2:5][O:1][C:2]2=[O:6])[CH2:25][CH2:26][C:27]2[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=2)=[CH:43][CH:42]=1)=[O:45]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 739492-OxazolidinoneHCID 59437417Methyl 4-{(4E)-5-{2-[(5-chloropentyl)oxy]phenyl}-3-[4-(methoxycarbonyl)benzyl]pent-4-en-1-yl}benzoate

Product 1

HCID 59437425Methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-(2-{[5-(2-oxo-1,3-oxazolidin-3-yl)pentyl]oxy}-phenyl)pent-4-en-1-yl]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 16.7 mg (0.19 mmol) of 2-oxazolidinone [CAS Reg. No. 497-25-6] is initially charged in 1.0 ml of dry DMF, and 7.9 mg (0.196 mmol) of sodium hydride (60% in paraffin oil) are added. The mixture is stirred at room temperature for 45 min. The reaction solution is then cooled to 0° C. and a solution of 30 mg (0.055 mmol) of methyl 4-{(4E)-5-{2-[(5-chloropentyl)oxy]phenyl}-3-[4-(methoxycarbonyl)benzyl]pent-4-en-1-yl}benzoate (racemate; Example 32A) in 0.5 ml of dry DMF is added. The mixture is stirred at room temperature for 1.5 h. The reaction solution is then carefully poured into 5 ml of ice-cold 10% strength ammonium chloride solution. The mixture is extracted twice with dichloromethane. The combined organic phases are dried over sodium sulfate, filtered and concentrated. This gives 25 mg (0.042 mmol, 76% of theory) of a colorless oil which is reacted without further purification.

Workup

  1. temperatureThe reaction solution is then cooled to 0° C.
  2. stirringThe mixture is stirred at room temperature for 1.5 h
  3. extractionThe mixture is extracted twice with dichloromethane
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThis gives 25 mg (0.042 mmol, 76% of theory) of a colorless oil which is reacted without further purification

Sources & evidence

ORD record
ord-838d21b0068c4faf80622da0ff21b4a2
Source dataset
uspto-grants-2012_07
Patent number
US08217063B2

Reaction notes

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