Phosphate → HCID 131711946, compound

HRID 345246Notes

Reaction equation

HRID 345246 reaction equation
O1CCCCC1[N:7]1[C@@H:10]([CH2:11][CH2:12][O:13]C2CCCCO2)[C@H:9]([CH2:20][CH2:21][O:22][O:23][C:24]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:25])[C:8]1=[O:36].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.P([O-])([O-])([O-])=O>CO>[N+:33]([C:30]1[CH:29]=[CH:28][C:27]([CH2:26][C:24]([O:23][O:22][CH2:21][CH2:20][C@H:9]2[C@H:10]([CH2:11][CH2:12][OH:13])[NH:7][C:8]2=[O:36])=[O:25])=[CH:32][CH:31]=1)([O-:35])=[O:34]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 521998p-Toluenesulfonic acid monohydrateHCID 131711947HCID 131711947, compound

Product 1

HCID 131711946HCID 131711946, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of trans-1-(2-tetrahydropyranyl)-3-(1-p-nitrobenzylcarbonyldioxyethyl)-4-[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 1M pH7 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-(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-d8e344c204534054839862f8655f9f15
Source dataset
uspto-grants-1991_10
Patent number
US05055573

Reaction notes

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