Diethyl Ether → HCID 131710127, compound

HRID 1604923Notes

Reaction equation

HRID 1604923 reaction equation
Cl[CH:2](Cl)[C:3]([O:5][CH2:6][C:7]1[CH2:8][S:9][C@@H:10]2[C@H:17]([NH:18][C:19](=[O:26])[CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[C:16](=[O:27])[N:11]2[C:12]=1[C:13]([OH:15])=[O:14])=O.CCOCC>C(O)C.C(OCC)(=O)C>[CH2:3]([O:5][CH2:6][C:7]1[CH2:8][S:9][C@@H:10]2[C@H:17]([NH:18][C:19](=[O:26])[CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[C:16](=[O:27])[N:11]2[C:12]=1[C:13]([OH:15])=[O:14])[CH3:2]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 131710126HCID 131710126, compound

Product 1

HCID 131710127HCID 131710127, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

3-Dichloroacetoxymethyl-7β-(2'-thienylacetamido)ceph-3-em-4-carboxylic acid (4.74 g.) was refluxed in ethanol (175 ml.) for 60 minutes; the mixture was filtered and the filtrate evaporated to give an oil. Trituration with ethyl acetate gave a solid (354 mg.), which was discarded. The ethyl acetate solution was extracted with sodium bicarbonate solution; the aqueous layer was then acidified and extracted with ethyl acetate. On drying and evaporation this solution gave a gum (3.34 g.), which was redissolved in hot ethyl acetate. Addition of a fourfold volume of ether gave a solid, which was discarded. The filtrate was concentrated and set aside at 0°; a white solid (548 mg.) crystallised out, m.p. 160°-165° (decomp.), [α]D25 = 157° (c 0.7, tetrahydrofuran) λλmax (NaHCO3 solution) 237nm (ε = 12,800), 260nm (ε = 8,000), νmax (CHBr3) 1770 (β-lactam), 1720 (COOH), 1659 and 1678 cm-1 (CONH). N.M.R. spectrum (D2O, with sodium bicarbonate) -O-CH2.CH3 systems centred at 6.5 and 8.83τ. (Found: C, 50.6; H, 4.8; N, 7.1; S, 16.3. C16H18N2O5S 2 requires C, 50.2; H, 4.7; N, 7.4; S, 16.8%). RF = 1.5 (System C), 1.35 (System B).

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate evaporated
  3. customto give an oil
  4. extractionThe ethyl acetate solution was extracted with sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. customOn drying
  7. customevaporation this solution
  8. customgave a gum (3.34 g.), which
  9. customgave a solid, which
  10. concentrationThe filtrate was concentrated
  11. customset aside at 0°
  12. customa white solid (548 mg.) crystallised out

Sources & evidence

ORD record
ord-0b98c2dc008c40729c5a7f584348a8ea
Source dataset
uspto-grants-1976_04
Patent number
US03948906

Reaction notes

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