15-Crown-5 → HCID 53848801, compound

HRID 1065529Notes

Reaction equation

HRID 1065529 reaction equation
[C:1]([O-:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[Na+].[I-].[C:9](=[N:12][O:13][N+]1(C)CCCCC1)([CH3:11])[CH3:10].[CH2:21]1OCCOCCOCCOCCOC1>O>[C:9](=[N:12][O:13][CH2:21][O:5][C:1](=[O:6])[CH:2]([CH3:4])[OH:3])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 3633615-Crown-5HCID 20540824N-[(isopropylideneamino)oxy]-N-methyl-piperidinium iodideHCID 23666456Sodium Lactate

Product 1

HCID 53848801HCID 53848801, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.1 g of sodium lactate, 3.5 g of N-[(isopropylideneamino)oxy]-N-methyl-piperidinium iodide and 0.1 g of 15-crown-5 in 10 ml of diglycol dimethyl ether are heated at 110° C. under nitrogen for 4 hours. The mixture is then poured into 50 ml of water and extracted three times with ethyl acetate. The organic phase is washed four times with water and subsequently evaporated. After chromatograhy of the residue on a 10-fold amount of silica gel with n-hexane/ethyl acetate (1:1) and evaporation of the eluate, there is obtained 0.35 g of L (-)-lactic acid [[(isopropylideneamino)oxy]methyl] ester; [α]D20 =-1.2° (c=1.50% in chloroform).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe organic phase is washed four times with water
  3. customsubsequently evaporated
  4. customAfter chromatograhy of the residue on a 10-fold amount of silica gel with n-hexane/ethyl acetate (1:1) and evaporation of the eluate

Sources & evidence

ORD record
ord-308105dff04a4e198aeb9259c018d415
Source dataset
uspto-grants-1982_05
Patent number
US04329488

Reaction notes

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