2-Methoxypropene → HCID 15549886, compound

HRID 975277Notes

Reaction equation

HRID 975277 reaction equation
[CH:1]1([C@H:4]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@@H:5]([OH:10])[C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1.[C:19](OC)([CH3:21])=[CH2:20].[NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1>C1C=CC=CC=1>[C:15]([O:14][C:12]([N:11]1[C@@H:4]([CH:1]2[CH2:3][CH2:2]2)[C@H:5]([C:6]([O:8][CH3:9])=[O:7])[O:10][C:19]1([CH3:21])[CH3:20])=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 83002-Methoxypropene2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 15549885HCID 15549885, compound

Product 1

HCID 15549886HCID 15549886, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2.63 g of methyl (2R,3S)-3-cyclopropyl-3-tert-butoxycarbonylamino-2-hydroxypropionate in 60 ml of benzene are added 1.94 ml of isopropenylmethylether and 0.25 g of p-toluenesulfonic acid pyridinium salt. The mixture is stirred at room temperature for one hour, and then refluxed for 40 minutes. After the mixture is cooled, 1.94 ml of isopropenylmethylether is added to the reaction mixture. The mixture is stirred at room temperature for 10 minutes, refluxed for 40 minutes, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=8:1) to give 2.69 g of methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-cyclopropyl-5-oxazolidinecarboxylate.

Workup

  1. temperaturerefluxed for 40 minutes
  2. temperatureAfter the mixture is cooled
  3. stirringThe mixture is stirred at room temperature for 10 minutes
  4. temperaturerefluxed for 40 minutes
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-5d9bd2e781c54f68a6854f15e7b9f0d8
Source dataset
uspto-grants-1997_03
Patent number
US05608073

Reaction notes

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