p-Toluenesulfonic acid → HCID 13127405, compound

HRID 1283144Notes

Reaction equation

HRID 1283144 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][C@@H:13]1[C:47](=[O:48])[N:15]2[C:16]([C:31]([O:33][CH:34]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])=[C:17]([CH2:20][O:21][C:22](=[O:30])[NH:23]C(=O)C(Cl)(Cl)Cl)[CH2:18][S:19][C@H:14]12.C(=O)(O)[O-].[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(Cl)(=O)C.ClCCl>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([OH:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[NH2:12][C@@H:13]1[C:47](=[O:48])[N:15]2[C:16]([C:31]([O:33][CH:34]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])=[C:17]([CH2:20][O:21][C:22](=[O:30])[NH2:23])[CH2:18][S:19][C@H:14]12

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 70601870HCID 70601870, compound

Product 1

HCID 13127405HCID 13127405, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 6367Acetyl chlorideSolvent

Procedure

The toluene-p-sulphonic acid salt of diphenylmethyl (6R,7R)-7-amino-3-trichloroacetylcarbamoyloxymethylceph-3-em-4-carboxylate (17.2g, 22.7 mmole) was dissolved in a mixture of anhydrous methanol (900 ml) and acetyl chloride (45 ml) and left to stand at 20° for 5 hours. Removal of the solvent under reduced pressure gave an oil, which was dissolved in dichloromethane. This solution was shaken with aqueous sodium bicarbonate solution and then washed with water. Toluene-p-sulphonic acid monohydrate (4.3 g, 22.7 mmole) was added and the solvent was evaporated in vacuo. The residue was dissolved in hot isopropanol (ca. 150 ml) and the solution was poured into diisopropyl ether (ca. 600 ml). The precipitated solid was filtered off and dried in vacuo to give the title compound (8.9 g, 64%), m.p. 110° to 112°; [α]D21° -14° (c, 1.0 in CHCl3); λmaxEtOH 259 nm (ε 6,120) and λinf.EtOH 227 nm (ε 15,800).

Workup

  1. waitleft
  2. customRemoval of the solvent under reduced pressure
  3. customgave an oil, which
  4. washwashed with water
  5. customthe solvent was evaporated in vacuo
  6. dissolutionThe residue was dissolved in hot isopropanol (ca. 150 ml)
  7. additionthe solution was poured into diisopropyl ether (ca. 600 ml)
  8. filtrationThe precipitated solid was filtered off
  9. customdried in vacuo

Sources & evidence

ORD record
ord-abf04cb8459d4d6ebd294c7664a77048
Source dataset
uspto-grants-1976_08
Patent number
US03974153

Reaction notes

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