Methane → HCID 21426473, compound

HRID 258772Notes

Reaction equation

HRID 258772 reaction equation
[CH3:1][O:2][CH:3]1[S:7][C:6](=[S:8])[N:5]=[N:4]1.C(=O)(O)[O-].[Na+].[Na].C(O[CH2:19][C:20]1[CH2:27][S:26][CH:25]2[N:22]([C:23](=[O:38])[CH:24]2[NH:28][C:29](=[O:37])[CH2:30][C:31]2[S:32][C:33](=[O:36])[S:34][CH:35]=2)[C:21]=1[C:39]([OH:41])=[O:40])(=O)C.C.Cl>O.C(OCC)(=O)C>[C:39]([C:21]1[N:22]2[CH:25]([S:26][CH2:27][C:20]=1[CH2:19][S:8][C:6]1[S:7][C:3]([O:2][CH3:1])=[N:4][N:5]=1)[CH:24]([NH:28][C:29](=[O:37])[CH2:30][C:31]1[S:32][C:33](=[O:36])[S:34][CH:35]=1)[C:23]2=[O:38])([OH:41])=[O:40]

Participants

9

Reactant 6

HCID 297MethaneHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 21426457HCID 21426457, compoundHCID 88826506HCID 88826506, compound

Product 1

HCID 21426473HCID 21426473, compoundYield 10.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

5-Methoxy-2-thioxo-1,3,4-thiadiazoline (4.43 g.) and sodium bicarbonate (2.27 g.) in water (20 cc.) are added to the sodium salt of 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 (12.2 g.) in a buffer (100 cc.) of pH 6.5. The mixture is heated under a nitrogen atmosphere to 50° C., for 5 hours. It is allowed to cool and treated with decolourising charcoal. Ethyl acetate (100 cc.) is added and the mixture is brought to pH 2.5 by adding 5 N hydrochloric acid while stirring. The organic phase is separated off and the aqueous phase is again extracted with ethyl acetate (160 cc.). The combined organic extracts are dried over sodium sulphate, treated with decolourising charcoal and then concentrated to dryness under reduced pressure (20 mm.Hg). A residue (11.5 g.) is obtained, and is triturated with acetonitrile (8 cc.) and isopropyl ether (8 cc.). A solid (2.4 g.) is filtered off and recrystallised from acetonitrile (375 cc.) and isopropyl ether (400 cc.) to give 2-carboxy-3-[(5-methoxy-1,3,4-thiadiazol-2-yl)-thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (1.52 g.) m.p. 208° C.

Workup

  1. temperatureto cool
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is again extracted with ethyl acetate (160 cc.)
  4. dry with materialThe combined organic extracts are dried over sodium sulphate
  5. additiontreated with decolourising charcoal
  6. concentrationconcentrated to dryness under reduced pressure (20 mm.Hg)
  7. customA residue (11.5 g.) is obtained
  8. customis triturated with acetonitrile (8 cc.) and isopropyl ether (8 cc.)
  9. filtrationA solid (2.4 g.) is filtered off
  10. customrecrystallised from acetonitrile (375 cc.) and isopropyl ether (400 cc.)

Sources & evidence

ORD record
ord-7faf45f3e3e04b16a7c6e9116fcacb06
Source dataset
uspto-grants-1977_07
Patent number
US04034090

Reaction notes

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