Sodium Iodide → HCID 70615922, compound

HRID 1604927Notes

Reaction equation

HRID 1604927 reaction equation
Cl[CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[I-:37].[Na+]>CC(C)=O>[I:37][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 15715515HCID 15715515, compound

Product 1

HCID 70615922HCID 70615922, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Diphenylmethyl 3-chloromethyl-7β-(2'thienylacetamido)-ceph-3-em-4 -carboxylate (7.858 g., 14.5 mmole) was dissolved in acetone and reacted with sodium iodide (7.8 g., 50 mmole) in acetone (100 ml.) in the dark for 90 minutes. At the end of this time the solution was filtered and poured into water (750 ml.) containing sodium chloride and sodium thiosulphate. The oil was extracted with ether (4×), and the organic layer washed once with water and twice with brine, and dried and evaporated to a foam, which was crystallised from ethyl acetate (16 ml.) to give the title compound. The mother liquors were washed with sodium thiosulphate, water and brine, and were dried and evaporated to a foam (2.75 g., impure title compound, approx. 30% yield). Yield of crystalline material 60%, m.p. 155-161°C (decomp.), [α]D28 =86.3° (c 0.73; tetrahydrofuran), λmax. (ethanol) 290 nm. (ε 8,400), νmax. (Nujol) 1773 (β-lactam), 1717 (CO2R), and 1670 and 1520 cm.-1 (-CONH-), N.M.R. (deuterochloroform) τ5.70 (2-proton broad singlet) (CH2I) (Found: C, 51.6; H, 3.7; I, 19.7; N, 4.3; S, 10.2. C27H23IN2O4S2 requires C, 51.3; H, 3.7; I, 20.1; N, 4.4; S, 10.2), RF 0.65 (Kieselgel G, benzene-ethylacetate=5:1) (T.L.C.).

Workup

  1. filtrationAt the end of this time the solution was filtered
  2. additionpoured into water (750 ml.)
  3. additioncontaining sodium chloride and sodium thiosulphate
  4. extractionThe oil was extracted with ether (4×)
  5. washthe organic layer washed once with water and twice with brine
  6. customdried
  7. customevaporated to a foam, which
  8. customwas crystallised from ethyl acetate (16 ml.)

Sources & evidence

ORD record
ord-128ebbfb41a9422db088159dd3879cc7
Source dataset
uspto-grants-1976_04
Patent number
US03948906

Reaction notes

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