p-Toluenesulfonic acid → HCID 178494566, compound

HRID 1654633Notes

Reaction equation

HRID 1654633 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][C:13]1[S:14][CH:15]=[C:16](/[C:18](=[N:46]/[OH:47])/[C:19]([NH:21][CH:22]2[C:44](=[O:45])[N:24]3[C:25]([C:32]([O:34][CH:35]([O:37][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])[CH3:36])=[O:33])=[C:26]([CH2:29][O:30][CH3:31])[CH2:27][S:28][C@H:23]23)=[O:20])[N:17]=1.C(OC(C)C)(C)C>CC(C)=O>[C:3]1([CH3:13])[C:4]([S:7]([OH:10])(=[O:8])=[O:9])=[CH:5][CH:6]=[CH:1][CH:2]=1.[NH2:12][C:13]1[S:14][CH:15]=[C:16](/[C:18](=[N:46]/[OH:47])/[C:19]([NH:21][CH:22]2[C:44](=[O:45])[N:24]3[C:25]([C:32]([O:34][CH:35]([O:37][C:38](=[O:43])[C:39]([CH3:41])([CH3:42])[CH3:40])[CH3:36])=[O:33])=[C:26]([CH2:29][O:30][CH3:31])[CH2:27][S:28][C@H:23]23)=[O:20])[N:17]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7914Diisopropyl EtherHCID 14459633HCID 14459633, compound

Product 1

HCID 178494566HCID 178494566, compoundYield 177.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 1.8 g (15 mmol) of p-toluenesulfonic acid in 5 ml of acetone was added dropwise to a solution of 5 g (9.3 mmol) of α-(2,2-dimethylpropanoyloxy)ethyl 7-[2-(2-aminothiazol-4-yl)-2-(Z)-hydroxyimino-acetamido]-3-methoxymethyl-3-cephem-4-carboxylate in 35 ml of acetone. After stirring briefly, a thick precipitate formed. After stirring for 15 minutes, a total of 185 ml of diisopropyl ether were slowly added dropwise to complete crystallization and the mixture was stirred for a short time. The precipitate was then filtered off with suction, washed with a little diisopropyl ether and dried in vacuo over calcium chloride/paraffin. 5.9 g of crystalline title compound were obtained, which consisted of an approximately 1:1 mixture of the two diastereomers according to HPLC and was identical in its physical and chemical properties with the product from working example 2.

Workup

  1. customa thick precipitate formed
  2. stirringAfter stirring for 15 minutes
  3. customcrystallization
  4. stirringthe mixture was stirred for a short time
  5. filtrationThe precipitate was then filtered off with suction
  6. washwashed with a little diisopropyl ether
  7. dry with materialdried in vacuo over calcium chloride/paraffin

Sources & evidence

ORD record
ord-3d8cec03c33e4b099ab3d970183b941b
Source dataset
uspto-grants-1995_04
Patent number
US05409918

Reaction notes

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