p-Toluenesulfonic acid → HCID 178494566, compound

HRID 1654634Notes

Reaction equation

HRID 1654634 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.COC(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 15413tert-Butyl methyl etherHCID 14459633HCID 14459633, compound

Product 1

HCID 178494566HCID 178494566, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 2.1 g (11 mmol) of p-toluenesulfonic acid in 5 ml of acetone was added dropwise to a solution of 5 g (9.3mmol) 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 precipitate formed, which process was completed by slowly adding 250 ml of t-butyl methyl ether. After stirring for 15 minutes, the crystalline product was filtered off with suction, washed with a little t-butyl methyl ether and dried in vacuo over calcium chloride/paraffin. 4.6 g of the desired crystalline title compound were obtained, which consisted of an approximately 1:1 ratio of the two diastereomers and was identical in its physical and chemical properties with the product from working example 2.

Workup

  1. customa precipitate formed
  2. stirringAfter stirring for 15 minutes
  3. filtrationthe crystalline product was filtered off with suction
  4. washwashed with a little t-butyl methyl ether
  5. dry with materialdried in vacuo over calcium chloride/paraffin

Sources & evidence

ORD record
ord-26332c79312540dbb5efe3a51a652d4c
Source dataset
uspto-grants-1995_04
Patent number
US05409918

Reaction notes

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