Sodium Bicarbonate → HCID 178520377, compound

HRID 258777Notes

Reaction equation

HRID 258777 reaction equation
C(=O)(O)[O-].[Na+].[S:6]=[C:7]1[NH:11][CH2:10][N:9]=[N:8]1.C(O[CH2:16][C:17]1[CH2:24][S:23][CH:22]2[N:19]([C:20](=[O:35])[CH:21]2[NH:25][C:26](=[O:34])[CH2:27][C:28]2[S:29][C:30](=[O:33])[S:31][CH:32]=2)[C:18]=1[C:36]([OH:38])=[O:37])(=O)C>>[C:36]([C:18]1[N:19]2[CH:22]([S:23][CH2:24][C:17]=1[CH2:16][S:6][C:7]1[N:11]=[CH:10][NH:9][N:8]=1)[CH:21]([NH:25][C:26](=[O:34])[CH2:27][C:28]1[S:29][C:30](=[O:33])[S:31][CH:32]=1)[C:20]2=[O:35])([OH:38])=[O:37]

Participants

4

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 30343333H-1,2,4-Triazole-3-thione, 4,5-dihydro-HCID 21426457HCID 21426457, compound

Product 1

HCID 178520377HCID 178520377, compoundYield 20.5%

Conditions

Temperature
60 °C

Procedure

Sodium bicarbonate (5.55 g.) and 3-thioxo-1,2,4-triazoline (3.63 g.) are added to 3-acetoxymethyl-2-carboxy-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (12.9 g.) in a buffer (250 cc.) of pH 6.4. The mixture is heated to 60° C. for 7 hours. It is allowed to cool, sodium bicarbonate (1 g.) is added and the mixture is washed with ethyl acetate (250 cc.), which is discarded. The aqueous solution is treated with decolourising charcoal and is acidified to pH 2 by adding 4 N hydrochloric acid in the presence of ethyl acetate (200 cc.). The organic phase is separated off and the aqueous phase is then extracted with ethyl acetate (750 cc.). The combined organic extracts are dried over sodium sulphate, treated with decolourising charcoal and concentrated to dryness under reduced pressure (20 mm Hg). A residue (5.5 g.) is obtained, which is triturated with acetonitrile (25 cc.). The solid is filtered off and washed with acetonitrile (25 cc.) and isopropyl ether (20 cc.) to give 2-carboxy-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-3-[(1,2,4-triazol-3-yl)-thiomethyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (2.9 g.), m.p. 227° C. (decomposition).

Workup

  1. temperatureto cool
  2. washthe mixture is washed with ethyl acetate (250 cc.), which
  3. additionThe aqueous solution is treated with decolourising charcoal
  4. additionby adding 4 N hydrochloric acid in the presence of ethyl acetate (200 cc.)
  5. customThe organic phase is separated off
  6. extractionthe aqueous phase is then extracted with ethyl acetate (750 cc.)
  7. dry with materialThe combined organic extracts are dried over sodium sulphate
  8. additiontreated with decolourising charcoal
  9. concentrationconcentrated to dryness under reduced pressure (20 mm Hg)
  10. customA residue (5.5 g.) is obtained
  11. customwhich is triturated with acetonitrile (25 cc.)
  12. filtrationThe solid is filtered off
  13. washwashed with acetonitrile (25 cc.) and isopropyl ether (20 cc.)

Sources & evidence

ORD record
ord-21a754d543f34a99bb93b9af9451e422
Source dataset
uspto-grants-1977_07
Patent number
US04034090

Reaction notes

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