HCID 70603475, compound → HCID 15742496, compound

HRID 2420574Notes

Reaction equation

HRID 2420574 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]([C:12]([OH:14])=[O:13])[N:10]2[C:15](=[O:26])[C@@H:16]([NH:17][C:18](=[O:25])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C@H:9]2[S:8][CH:7]=1)(=O)C>O>[OH:4][CH2:5][C:6]1[CH:11]([C:12]([OH:14])=[O:13])[N:10]2[C:15](=[O:26])[C@@H:16]([NH:17][C:18](=[O:25])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C@H:9]2[S:8][CH:7]=1

Participants

3

Reactant 1

HCID 70603475HCID 70603475, compound

Product 1

HCID 15742496HCID 15742496, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 3-acetoxymethyl-7β-(2-thienylacetamido)ceph-2-em-4-carboxylic acid (42 g.) in water (400 ml.) was flushed with nitrogen and potassium carbonate (43 g.) added. The mixture was treated with water (200 ml.) to effect complete solution and methanol (50 ml.) added. The solution was stored at 37° for 4.25 hours and then at 22° for 17 hours. The methanol was removed in vacuo and the mixture diluted with water (200 ml.) and stirred with ethyl acetate (800 ml.). The pH of the mixture was adjusted to 2.5 with orthophosphoric acid and the organic layer separated and washed with water and dried. The ethyl acetate was evaporated in vacuo until crystallisation of the product started, and the mixture cooled. Filtration gave the title compound (19.7 g., 52.5%) as fine needles, m.p. 151.5°-152° (decomp), [α]D + 465° (tetrahydrofuran), λmax. 234 nm. (ε 14,400), νmax. 3250 (NH and bonded OH), 2600 and 1725 (CO2H), 1755 (β-lactam) and 1650 and 1520 cm-1 (CONH), τ (D2O-sodium bicarbonate) 2.65 and 3.0 (thienyl, 3-proton complex), 3.7 (C(2) -H), broad s), 4.62 (C(2) -H, d, J 4.5 Hz), 4.74 (C(6) -H, d, J 4.5 Hz), 5.15 (C(4) -H, broad s), 5.8 (CH2OH, broad s) and 6.12(CH2CONH, s). (Found: C, 47.4; H, 4.05; N, 7.65; s 18.0; Calc. for C14H14N2O5S2 : C, 47.5; H, 3.9; N, 7.9; S, 18.1%).

Workup

  1. customwas flushed with nitrogen and potassium carbonate (43 g.)
  2. additionadded
  3. additionThe mixture was treated with water (200 ml.)
  4. additionadded
  5. waitat 22° for 17 hours
  6. customThe methanol was removed in vacuo
  7. additionthe mixture diluted with water (200 ml.)
  8. customthe organic layer separated
  9. washwashed with water
  10. customdried
  11. customThe ethyl acetate was evaporated in vacuo until crystallisation of the product
  12. temperaturethe mixture cooled
  13. filtrationFiltration

Sources & evidence

ORD record
ord-3f801e4b371745b68e15cc2828248e6f
Source dataset
uspto-grants-1978_08
Patent number
US04110534

Reaction notes

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