2-Methoxypropene → HCID 57198355, compound

HRID 2293786Notes

Reaction equation

HRID 2293786 reaction equation
[C:1]1([C@H:7]([NH:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:8]([OH:11])[CH:9]=[CH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[C:23]([CH3:25])=[CH2:24].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C=CC=CC=1.ClCCl>[CH:9]([C@H:8]1[O:11][C:23]([CH3:25])([CH3:24])[N:12]([C:13](=[O:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[CH2:10]

Participants

6

Reactant 3

HCID 83002-MethoxypropeneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57161994HCID 57161994, compound

Product 1

HCID 57198355HCID 57198355, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

32 mg (0.12 mmol) of (1S,2R)-1-phenyl-1-benzoylamino-2-hydroxy-3-butene, in suspension in 0.64 cm3 of anhydrous toluene, are put, under an argon atmosphere, in a 10 cm3 single-necked, round-bottomed flask equipped with a magnetic stirrer system and a reflux condenser. 226 μl (173 mg, 2.4 mmol) of 2-methoxypropene, 6.0 mg (0.024 mmol) of pyridinium p-toluenesulphonate and 8 grains of 4 Å molecular sieve are then added. The resulting reaction mixture is allowed to react at a temperature in the region of 15° C. for 2.5 hours and is then heated at 100° C. for 2 hours. After cooling to a temperature in the region of 15° C., the reaction mixture is diluted in 40 cm3 of dichloromethane. The organic phase is washed once with 5 cm3 of a saturated sodium bicarbonate solution, 3 times with 5 cm3 of water and once with a saturated aqueous sodium chloride solution and is then dried over anhydrous sodium sulphate. After filtration and concentration to dryness under reduced pressure, the residue obtained is purified by chromatography on silica gel, eluting a first time with an ethyl ether/dichloromethane (2/98 by volume) mixture and then a second time with an ethyl acetate/hexane (10/90 by volume) mixture. There are thus obtained, with a yield of 38%, 14 mg (0.0456 mmol) of (4S,5R)-5-vinyl-3-benzoyl-2,2-dimethyl-4-phenyl-1,3-oxazolidine, the characteristics of which are the following:

Workup

  1. customround-bottomed flask equipped with a magnetic stirrer system and a reflux condenser
  2. customThe resulting reaction mixture
  3. customto react at a temperature in the region of 15° C. for 2.5 hours
  4. temperatureAfter cooling to a temperature in the region of 15° C.
  5. washThe organic phase is washed once with 5 cm3 of a saturated sodium bicarbonate solution, 3 times with 5 cm3 of water and once with a saturated aqueous sodium chloride solution
  6. dry with materialis then dried over anhydrous sodium sulphate
  7. filtrationAfter filtration and concentration to dryness under reduced pressure
  8. customthe residue obtained
  9. customis purified by chromatography on silica gel
  10. washeluting a first time with an ethyl ether/dichloromethane (2/98 by volume) mixture

Sources & evidence

ORD record
ord-3ad96336f012412cbf65fe0a6fc056de
Source dataset
uspto-grants-1997_11
Patent number
US05686623

Reaction notes

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