Toluene → HCID 57020377, compound

HRID 2293785Notes

Reaction equation

HRID 2293785 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@H:10]([OH:15])[C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]1(C)[CH:27]=CC=C[CH:23]=1.COC(C)=C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[C:1]([O:5][C:6]([N:8]1[C@@H:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C@@H:10]([C:11]([O:13][CH3:14])=[O:12])[O:15][C:22]1([CH3:27])[CH3:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1140TolueneHCID 83002-MethoxypropeneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10517954HCID 10517954, compound

Product 1

HCID 57020377HCID 57020377, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

147.5 mg (0.50 mmol) of methyl (2S,3S)-3-t-butoxycarbonylamino-3-phenyl-2-hydroxypropionate and 2.5 cm3 of anhydrous toluene are introduced, under an argon atmosphere, into a 10 cm3 round-bottomed flask equipped with a magnetic stirrer system. 10 grains of 4 Åmolecular sieve, 188.5 μl (144.2 mg, 2.0 mmol) of 2-methoxypropene and 12.5 mg (0.05 mmol) of pyridinium p-toluenesulphonate are then added to the suspension obtained. The mixture is allowed to react for 1 hour at a temperature in the region of 20° C. and is then heated to 120° C. and allowed to react at this temperature for 2 hours. The resulting dark-brown reaction mixture is cooled to a temperature in the region of 20° C. 60 cm3 of dichloromethane are added. The organic phase is washed with 5 cm3 of a saturated aqueous sodium hydrogen-carbonate solution, 3 times with 5 cm3 of water and then once with 5 cm3 of a saturated aqueous sodium chloride solution. The organic phase is dried over anhydrous sodium sulphate. After filtration and concentration to dryness under reduced pressure, a residue is obtained which is chromatographed on a column of silica gel, eluting with an ethyl ether/hexane (15/85 by volume) mixture. There are obtained, with a yield of 36%, 60 mg (0.18 mmol) of (4S,5S)-3-t-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-methoxycarbonyl-1,3-oxazolidine, the characteristics of which are the following:

Workup

  1. customequipped with a magnetic stirrer system
  2. customobtained
  3. customto react for 1 hour at a temperature in the region of 20° C.
  4. customto react at this temperature for 2 hours
  5. temperatureThe resulting dark-brown reaction mixture is cooled to a temperature in the region of 20° C
  6. washThe organic phase is washed with 5 cm3 of a saturated aqueous sodium hydrogen-carbonate solution, 3 times with 5 cm3 of water
  7. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  8. filtrationAfter filtration and concentration to dryness under reduced pressure
  9. customa residue is obtained which
  10. customis chromatographed on a column of silica gel
  11. washeluting with an ethyl ether/hexane (15/85 by volume) mixture

Sources & evidence

ORD record
ord-30773e612afe4159977afc3f2140df88
Source dataset
uspto-grants-1997_11
Patent number
US05686623

Reaction notes

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