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

HRID 1657425Notes

Reaction equation

HRID 1657425 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-4705d4b946dc4654a4694c29e7f67396
Source dataset
uspto-grants-1976_06
Patent number
US03960852

Reaction notes

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