Dicyclohexylcarbodiimide → HCID 68147853, compound

HRID 267490Notes

Reaction equation

HRID 267490 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.[F:27][C:28]([F:36])([F:35])[S:29]([CH2:31][C:32](O)=[O:33])=[O:30].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[F:27][C:28]([F:36])([F:35])[S:29]([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]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 12098365Benzhydryl 7-amino-3-cephem-4-carboxylateHCID 234231292408-16-4

Product 1

HCID 68147853HCID 68147853, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.78 g (2 mmol) of benzhydryl 7-amino-3-cephem-4-carboxylate (South African Pat. No. 71/06719), 0.35 g (2 mmol) of trifluoromethylsulfinylacetic acid and 0.4 g (2 mmol) of dicyclohexylcarbodiimide 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 percent aqueous sodium bicarbonate. 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 percent aqueous sodium bicarbonate
  8. customthe precipitated product is collected
  9. customdried

Sources & evidence

ORD record
ord-19506bbe1c5848eaa93e42d8388262b1
Source dataset
uspto-grants-1976_03
Patent number
US03943127

Reaction notes

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