Water → HCID 178494566, compound

HRID 1654631Notes

Reaction equation

HRID 1654631 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.O>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 962WaterHCID 6101p-Toluenesulfonic acidHCID 14459633HCID 14459633, compound

Product 1

HCID 178494566HCID 178494566, compoundYield 151.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 570 mg (3 mmol) of p-toluenesulfonic acid in 1 ml of acetone was added to a solution of 1.08 g (2 mmol) of α-(2,2-dimethylpropanoyloxy)ethyl 7-[2-(2-aminothiazol-4-yl)-2-(Z)-hydroxyimino-acetamido]-3-methoxymethyl-3-cephem-4-carboxylate in 3 ml of acetone. 28 ml of water was then slowly added dropwise with stirring to the rapidly forming crystal suspension. The crystalline precipitate was then filtered off with suction, washed eight times with 3 ml of water and dried in vacuo over calcium chloride/paraffin. 1.08 g of the desired title compound were obtained, which consisted of an approximately 1:1 mixture of the two diastereomers according to HPLC and was characterized as crystalline under the polarization microscope. M.p.: from 190° C. (with decomposition).

Workup

  1. customrapidly forming crystal suspension
  2. filtrationThe crystalline precipitate was then filtered off with suction
  3. washwashed eight times with 3 ml of water
  4. dry with materialdried in vacuo over calcium chloride/paraffin

Sources & evidence

ORD record
ord-a7e4047585da47578af8395b8ca69ead
Source dataset
uspto-grants-1995_04
Patent number
US05409918

Reaction notes

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