Diisopropyl Ether → HCID 21426472, compound

HRID 258775Notes

Reaction equation

HRID 258775 reaction equation
[Na].C(O[CH2:6][C:7]1[CH2:14][S:13][CH:12]2[N:9]([C:10](=[O:25])[CH:11]2[NH:15][C:16](=[O:24])[CH2:17][C:18]2[S:19][C:20](=[O:23])[S:21][CH:22]=2)[C:8]=1[C:26]([OH:28])=[O:27])(=O)C.[S-]C#N.[K+].C(=O)(O)[O-].[Na+].[C:38]1([N:44]2[C:48](=[S:49])[NH:47][N:46]=[N:45]2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(OC(C)C)(C)C>O.O1CCCC1>[C:26]([C:8]1[N:9]2[CH:12]([S:13][CH2:14][C:7]=1[CH2:6][S:49][C:48]1[N:44]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:45]=[N:46][N:47]=1)[CH:11]([NH:15][C:16](=[O:24])[CH2:17][C:18]1[S:19][C:20](=[O:23])[S:21][CH:22]=1)[C:10]2=[O:25])([OH:28])=[O:27]

Participants

9

Reactant 6

HCID 7914Diisopropyl EtherHCID 516872Potassium thiocyanateHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 21426457HCID 21426457, compoundHCID 178527916HCID 178527916, compound

Product 1

HCID 21426472HCID 21426472, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

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 (10 g.) is dissolved in water (51 cc.). Potassium thiocyanate (60 g.), sodium bicarbonate (2.24 g.) and 1-phenyl-5-thioxo-1,2,3,4-tetrazoline (4.75 g.) are added to this solution and the mixture is heated to 60° C. for 8 hours. After cooling, the reaction mixture is diluted with water (250 cc.) and washed with ethyl acetate (200 cc.) after acidification to pH 5.5 by adding 4 N hydrochloric acid. The mixture is then acidified to pH 1.5 by adding 4 N hydrochloric acid in the presence of ethyl acetate (100 cc.). After decanting the organic phase, the aqueous phase is extracted four times with ethyl acetate (a total of 400 cc.). The organic extracts are combined, washed three times with an 0.1 N hydrochloric acid solution (a total of 300 cc.) and then twice with water (a total of 300 cc.), dried over sodium sulphate, treated with decolourising charcoal, filtered and then concentrated to dryness under reduced pressure (20 mm Hg). The residue obtained is dissolved in tetrahydrofuran (50 cc.) and this solution is then added to isopropyl ether (1 liter). A product precipitates, which is isolated by filtration and dried under reduced pressure (0.1 mm Hg). 2-Carboxy-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-3-[(1-phenyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]- 5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (5.4 g.) is thus obtained.

Workup

  1. temperatureAfter cooling
  2. washwashed with ethyl acetate (200 cc.) after acidification to pH 5.5
  3. additionby adding 4 N hydrochloric acid
  4. additionby adding 4 N hydrochloric acid in the presence of ethyl acetate (100 cc.)
  5. customAfter decanting the organic phase
  6. extractionthe aqueous phase is extracted four times with ethyl acetate (a total of 400 cc
  7. washwashed three times with an 0.1 N hydrochloric acid solution (a total of 300 cc
  8. dry with material), dried over sodium sulphate
  9. additiontreated with decolourising charcoal
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure (20 mm Hg)
  12. customThe residue obtained
  13. customA product precipitates
  14. customwhich is isolated by filtration
  15. customdried under reduced pressure (0.1 mm Hg)

Sources & evidence

ORD record
ord-0dd15a0a469f4b86af5bccf3b42e1a0c
Source dataset
uspto-grants-1977_07
Patent number
US04034090

Reaction notes

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