Acetone → HCID 70635824, compound

HRID 596827Notes

Reaction equation

HRID 596827 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[CH:13]([C:23]([O:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[C:14]([C:17]([O:19][CH2:20][CH2:21]Br)=[O:18])=[CH:15][S:16][C@H:11]12)=[O:8].[I-].[Na+].CC(C)=O.S1C=CC=C1CC(NC1S[C@@H]2CC(=O)N2C(C([O-])=O)C=1C(OCC[I:67])=O)=O>C(Cl)(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[CH:13]([C:23]([O:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[C:14]([C:17]([O:19][CH2:20][CH2:21][I:67])=[O:18])=[CH:15][S:16][C@H:11]12)=[O:8]

Participants

6

Reactant 4

HCID 180AcetoneHCID 5238Sodium IodideHCID 70636258HCID 70636258, compoundHCID 131710671HCID 131710671, compound

Product 1

HCID 70635824HCID 70635824, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Benzhydryl 7-(2-thienylacetamido)-3-(2-bromoethoxycarbonyl)-2-cephem-4-carboxylate (7.61 g., 12 mmol.) was combined with sodium iodide (6.75 g., 45 meq.) in 100 ml. acetone. The reaction mixture was degassed and then heated to 35° with stirring for 16 hours. The reaction mixture was filtered and evaporated to dryness. The residue was dissolved in ethyl acetate and washed with water (3X) and brine and dried (Na2SO4). Evaporation in vacuo to dryness provided 7.78 g. (95.5%) of benzhydryl 7-(2-thienylacetamido-3-(2-iodoethoxycarbonyl)-2-cephem-4-carboxylate: ir (CHCl3) 1785 cm-1 (β-lactam C = O); nmr (CDCl2) δ 2.96 (t, 2, J = 7.0 Hz, --OCH2 --), 3.80 (s, 2, side chain CH2), 4.24 (t, 2, J = 7.0 Hz, --OCH2 --), 4.95 (d, 1, J = 4.0 Hz, C6 --H), 5.24 (q, 1, J = 4.0 Hz, C7 --H, rest of the signal covered by C4 --H), 5.50 (s, 1, C4 --H), and 7.80 (s, 1, C2 --H).

Workup

  1. customThe reaction mixture was degassed
  2. temperatureheated to 35°
  3. filtrationThe reaction mixture was filtered
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water (3X) and brine
  7. dry with materialdried (Na2SO4)
  8. customEvaporation in vacuo to dryness
  9. customprovided 7.78 g

Sources & evidence

ORD record
ord-b63d9c9734294cb2bf9963916ba22f47
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

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