Phosphate → 3-Phenylacetamido-4-(2-hydroxyethyl)-2-azetidinone

HRID 1278251Notes

Reaction equation

HRID 1278251 reaction equation
O1CCCCC1[N:7]1[CH:10]([CH2:11][CH2:12][O:13]C2CCCCO2)[CH:9]([NH:20][C:21](=[O:29])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:8]1=[O:30].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.P([O-])([O-])([O-])=O>CO>[C:23]1([CH2:22][C:21]([NH:20][CH:9]2[CH:10]([CH2:11][CH2:12][OH:13])[NH:7][C:8]2=[O:30])=[O:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 1061PhosphateHCID 521998p-Toluenesulfonic acid monohydrateHCID 541458371-(2-Tetrahydropyranyl)-3-phenylacetamido-4-[2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone

Product 1

HCID 128047363-Phenylacetamido-4-(2-hydroxyethyl)-2-azetidinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(2-tetrahydropyranyl)-3-phenylacetamido-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 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 3-phenylacetamido-4-(2-hydroxyethyl)-2-azetidinone.

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-a839712fa29b4df5a4f5d89a74e04615
Source dataset
uspto-grants-1981_07
Patent number
US04281002

Reaction notes

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