Propylene Oxide → HCID 131710487, compound

HRID 1287609Notes

Reaction equation

HRID 1287609 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][C:7]([CH2:8][O:9][C:10]([C:12]2[N:17]3[C:18](=[O:27])[CH:19]([NH:20][C:21](=[S:26])[CH2:22][CH2:23][C:24]#[N:25])[C@H:16]3[S:15][CH2:14][C:13]=2[OH:28])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].CC(N(C)C)=O.C1OC1C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([C:12]2[N:17]3[C:18](=[O:27])[CH:19]([NH:20][C:21](=[S:26])[CH2:22][CH2:23][C:24]#[N:25])[C@H:16]3[S:15][CH2:14][C:13]=2[O:28][S:42]([CH3:41])(=[O:44])=[O:43])=[O:11])=[CH:29][CH:30]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6378Propylene OxideHCID 31297Methanesulfonyl chlorideHCID 31374DimethylacetamideHCID 1317104857-Cyanomethylthioacetamido-3-cephem-3ol-4-carboxylic acid p-nitrobenzyl ester

Product 1

HCID 131710487HCID 131710487, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.5 g. of 7-cyanomethylthioacetamido-3-cephem-3ol-4-carboxylic acid p-nitrobenzyl ester in 25 ml. of dry dimethylacetamide is added 1 ml. of propylene oxide and one equivalent of methanesulfonyl chloride. After stirring for 4 hours, the mixture is taken up in ethyl acetate and washed with saturated sodium chloride solution. Solvent is removed from the ethyl acetate solution under reduced pressure and the residue is purified by thin layer chromatography yielding the product 7-cyanomethylthioacetamido-3-methylsulfonyloxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester as an amorphous solid.

Workup

  1. washwashed with saturated sodium chloride solution
  2. customSolvent is removed from the ethyl acetate solution under reduced pressure
  3. customthe residue is purified by thin layer chromatography

Sources & evidence

ORD record
ord-0f7d7b5080174c58acf657d6af1c5401
Source dataset
uspto-grants-1976_10
Patent number
US03985746

Reaction notes

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