Ethyl Acetate → HCID 88834472, compound

HRID 1605406Notes

Reaction equation

HRID 1605406 reaction equation
[OH:1][CH2:2][C:3]1[CH2:4][S:5](=[O:30])[C@@H:6]2[CH:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:17](=[O:29])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10].C(OCC)(=O)C>CC(C)=O>[CH:2]([C:3]1[CH2:4][S:5](=[O:30])[C@@H:6]2[CH:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:17](=[O:29])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10])=[O:1]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 68132076HCID 68132076, compound

Product 1

HCID 88834472HCID 88834472, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 0.843 g (1.7 mmole) of 2,2,2-trichloroethyl 3-hydroxymethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide in 50 ml of acetone at 0° is added over the period of about 2 min. 0.450 ml of 8N CrO3 in H2SO3 and the mixture is stirred at 0° for 5 min., then poured into a mixture of 300 ml ethyl acetate - 300 ml water and the ethyl acetate layer washed with water, dried (MgSO4), and evaporated in vacuo. The residue when chromatographed on silica gel with CHCl3 gives 2,2,2-trichloroethyl 3-formyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. washthe ethyl acetate layer washed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo
  4. customThe residue when chromatographed on silica gel with CHCl3

Sources & evidence

ORD record
ord-4abbefbf5d2d4976b164ea56ba68bbf1
Source dataset
uspto-grants-1976_04
Patent number
US03950329

Reaction notes

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