3,4-dihydro-2H-pyran → HCID 18648593, compound

HRID 467162Notes

Reaction equation

HRID 467162 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([N:9]1[CH2:15][CH2:14][CH2:13][C@H:10]1[CH2:11][OH:12])=[O:8].[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1>C(#N)C.C1(C)C(S(O)(=O)=O)=CC=CC=1.N1C=CC=CC=1>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([N:9]1[CH2:15][CH2:14][CH2:13][C@H:10]1[CH2:11][O:12][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][O:16]1)=[O:8]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 18648590HCID 18648590, compound

Product 1

HCID 18648593HCID 18648593, compoundYield 110%

Reagents, catalysts & solvents 2

HCID 22058245HCID 22058245, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

The thus obtained L-pyroglutamyl-L-prolinol (110 g, 0.519 mol) and dihydropyran (220 g, 2.62 mol) are dissolved in acetonitrile (2.75 l), and pyridine toluenesulfonate (11 g) is added under water-cooling. The mixture is stirred at room temperature for two days, and the reaction liquid is concentrated under reduced pressure, dissolved again in methylene chloride (1.5 l) and washed successively with 5% potassium carbonate (1 l) and water (1 l). The methylene chloride layer is dried over anhydrous magnesium sulfate and filtered. The filtrate is concentrated to dryness under reduced pressure to give N-pyroglutamyl-O-tetrahydropyranyl-L-prolinol (169 g, 110%).

Workup

  1. temperaturecooling
  2. customthe reaction liquid
  3. concentrationis concentrated under reduced pressure
  4. dissolutiondissolved again in methylene chloride (1.5 l)
  5. washwashed successively with 5% potassium carbonate (1 l) and water (1 l)
  6. dry with materialThe methylene chloride layer is dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ec7759caaa49419185756baaae8d22e9
Source dataset
uspto-grants-1992_10
Patent number
US05158970

Reaction notes

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