Diethyl Ether → HCID 88605859, compound

HRID 2108211Notes

Reaction equation

HRID 2108211 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C1(OC)C=CC=CC=1.C([NH:35][C:36]1[S:37][CH:38]=[C:39](/[C:41](=[N:73]/[O:74]CC2C=CC(OC)=CC=2OC)/[C:42]([NH:44][C@@H:45]2[C:71](=[O:72])[N:47]3[C:48]([C:59]([O:61]CC4C=CC(OC)=CC=4)=[O:60])=[C:49]([S:52]/[CH:53]=[CH:54]\[C:55]([O:57][CH3:58])=[O:56])[CH2:50][S:51][C@H:46]23)=[O:43])[N:40]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C>CCCCCC>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:35][C:36]1[S:37][CH:38]=[C:39](/[C:41](=[N:73]/[OH:74])/[C:42]([NH:44][C@@H:45]2[C:71](=[O:72])[N:47]3[C:48]([C:59]([OH:61])=[O:60])=[C:49]([S:52]/[CH:53]=[CH:54]\[C:55]([O:57][CH3:58])=[O:56])[CH2:50][S:51][C@H:46]23)=[O:43])[N:40]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 178500988HCID 178500988, compound

Product 1

HCID 88605859HCID 88605859, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of 3.5 ml of trifluoroacetic acid and 0.7 ml of anisole was added under ice-cooling 250 mg (0.25 mM) of 4-methoxybenzyl 7β-{2-(2-tritylaminothiazol-4yl)-2-[(Z)-2,4-dimethoxybenzyloxyimino]acetamido}-3-[(Z)-2-methoxycarbonylvinylthio]-3-cephem-4-carboxylate, and the mixture was stirred for 40 minutes and then at room temperature for 10 minutes. After the reaction, the reaction solution was slowly added dropwise to a mixture of diethyl ether and n-hexane (1:2, 30 ml), and the formed crystals were collected by filtration to give 150 mg of 7β-{2-(2-aminothiazol-4-yl)-2-[(Z)-hydroxyimino]acetamido}-3-[(Z)-2-methoxycarbonylvinylthio]-3-cephem-4-carboxylic acid trifluoroacetate.

Workup

  1. additionwas added under ice-
  2. waitat room temperature for 10 minutes
  3. customAfter the reaction
  4. filtrationthe formed crystals were collected by filtration

Sources & evidence

ORD record
ord-df333fd31cd94d3c9ffc69ecafb00c89
Source dataset
uspto-grants-1990_06
Patent number
US04937332

Reaction notes

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