Phosphate → HCID 131711853, compound

HRID 1856318Notes

Reaction equation

HRID 1856318 reaction equation
O1CCCCC1[N:7]1[C@@H:10]([CH:11]([CH3:20])[CH2:12][O:13]C2CCCCO2)[C@H:9]([CH2:21][CH2:22][O:23][O:24][C:25]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=2)=[O:26])[C:8]1=[O:37].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.P([O-])([O-])([O-])=O>CO>[N+:34]([C:31]1[CH:30]=[CH:29][C:28]([CH2:27][C:25]([O:24][O:23][CH2:22][CH2:21][C@H:9]2[C@H:10]([CH:11]([CH3:20])[CH2:12][OH:13])[NH:7][C:8]2=[O:37])=[O:26])=[CH:33][CH:32]=1)([O-:36])=[O:35]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 521998p-Toluenesulfonic acid monohydrateHCID 131711854HCID 131711854, compound

Product 1

HCID 131711853HCID 131711853, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of trans-1-(2-tetrahydropyranyl)-3-(1-p-nitrobenzylcarbonyldioxyethyl)-4-[1-methyl-2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone in methanol at 25° C. is treated with 0.1 molar equivalent of p-toluenesulfonic acid monohydrate. The solution is stirred for a period of 2 hours and then neutralized with 1 M pH 7 phosphate buffer. The product is extracted into ethyl acetate. The ethyl acetate solution is washed with brine, dried over magnesium sulfate and filtered. The filtrate is evaporated under reduced pressure to give trans-3-(1-p-nitrobenzylcarbonyldioxyethyl)-4-(1-methyl-2-hydroxyethyl)-2-azetidinone. The cis diastereoisomers are obtained in an analogous manner.

Workup

  1. extractionThe product is extracted into ethyl acetate
  2. washThe ethyl acetate solution is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-34705af447d4454f866a08bdcd71b230
Source dataset
uspto-grants-1980_08
Patent number
US04218462

Reaction notes

Loading…