Benzenesulfonic Acid → HCID 178494567, compound

HRID 1654630Notes

Reaction equation

HRID 1654630 reaction equation
[C:1]1([S:7]([OH:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[S:13][CH:14]=[C:15](/[C:17](=[N:45]/[OH:46])/[C:18]([NH:20][CH:21]2[C:43](=[O:44])[N:23]3[C:24]([C:31]([O:33][CH:34]([O:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[CH3:35])=[O:32])=[C:25]([CH2:28][O:29][CH3:30])[CH2:26][S:27][C@H:22]23)=[O:19])[N:16]=1>C(OCC)(=O)C>[C:1]1([S:7]([OH:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[S:13][CH:14]=[C:15](/[C:17](=[N:45]/[OH:46])/[C:18]([NH:20][CH:21]2[C:43](=[O:44])[N:23]3[C:24]([C:31]([O:33][CH:34]([O:36][C:37](=[O:42])[C:38]([CH3:40])([CH3:41])[CH3:39])[CH3:35])=[O:32])=[C:25]([CH2:28][O:29][CH3:30])[CH2:26][S:27][C@H:22]23)=[O:19])[N:16]=1

Participants

4

Reactant 2

HCID 7371Benzenesulfonic AcidHCID 14459633HCID 14459633, compound

Product 1

HCID 178494567HCID 178494567, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 0.44 g (1 eq. ) of benzenesulfonic acid in 9 ml of ethyl acetate was added dropwise to a solution of 1.5 g (2.77 mmol) of α-(2,2-dimethylpropanoyloxy)ethyl 7-[2-(2-aminothiazol-4-yl)-2-(Z)-hydroxyimino-acetamido]-3-methoxymethyl-3-cephem-4-carboxylate in 21 ml of ethyl acetate. After crystallization began, the mixture was stirred for a further 30 minutes, and the crystals were filtered off with suction and washed with a little diethyl ether. After drying over CaCl2 /paraffin in vacuo, 1.4 g of the desired title compound were obtained, which was identified as crystalline material under the polarization microscope and consisted of an approximately 1:1 mixture of the two diastereomers according to HPLC.

Workup

  1. customAfter crystallization
  2. filtrationthe crystals were filtered off with suction
  3. washwashed with a little diethyl ether
  4. dry with materialAfter drying over CaCl2 /paraffin in vacuo

Sources & evidence

ORD record
ord-8f1c923e5f0f4f87800b570ab4ede9f1
Source dataset
uspto-grants-1995_04
Patent number
US05409918

Reaction notes

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