Dicyclohexylcarbodiimide → 7-Methylsulfonylacetamido-3-cephem-4-carboxylic acid

HRID 1578877Notes

Reaction equation

HRID 1578877 reaction equation
[NH2:1][CH:2]1[C:25](=[O:26])[N:4]2[C:5]([C:9]([O:11]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:10])=[CH:6][CH2:7][S:8][C@H:3]12.[CH3:27][S:28]([CH2:31][C:32](O)=[O:33])(=[O:30])=[O:29].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH3:27][S:28]([CH2:31][C:32]([NH:1][CH:2]1[C:25](=[O:26])[N:4]2[C:5]([C:9]([OH:11])=[O:10])=[CH:6][CH2:7][S:8][C@H:3]12)=[O:33])(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 37328412-Methanesulfonylacetic acidHCID 12098365Benzhydryl 7-amino-3-cephem-4-carboxylate

Product 1

HCID 681478767-Methylsulfonylacetamido-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzhydryl 7-amino-3-cephem-4-carboxylate (0.78 g, 2 mmol), methylsulfonylacetic acid (0.27 g, 2 mmol), and dicyclohexylcarbodiimide (0.4 g, 2 mmol) in dry tetrahydrofuran (15 ml) is stirred at room temperature overnight. The precipitate is collected and washed with tetrahydrofuran and the combined filtrate and washings are evaporated in vacuo. The residue is treated with a cold solution of trifluoroacetic acid (10 ml) and anisole (0.5 g) for 15 minutes and then concentrated in vacuo. The residue is dissolved in ethyl acetate and treated with 5% NaHCO3. The aqueous phase is adjusted to pH 2 and the precipitated product is collected and dried.

Workup

  1. customThe precipitate is collected
  2. washwashed with tetrahydrofuran
  3. customthe combined filtrate and washings are evaporated in vacuo
  4. additionThe residue is treated with a cold solution of trifluoroacetic acid (10 ml) and anisole (0.5 g) for 15 minutes
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue is dissolved in ethyl acetate
  7. additiontreated with 5% NaHCO3
  8. customthe precipitated product is collected
  9. customdried

Sources & evidence

ORD record
ord-9a493ed1ecfb43f3bd1d1c7287ac657a
Source dataset
uspto-grants-1976_02
Patent number
US03939266

Reaction notes

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