Water → 2-Acetoxymethoxycarbonyl-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene

HRID 258782Notes

Reaction equation

HRID 258782 reaction equation
[Na].[C:2]([C:5]1[N:6]2[CH:9]([S:10][CH2:11][C:12]=1[CH2:13][S:14][C:15]1[N:19]([CH3:20])[N:18]=[N:17][N:16]=1)[CH:8]([NH:21][C:22](=[O:30])[CH2:23][C:24]1[S:25][C:26](=[O:29])[S:27][CH:28]=1)[C:7]2=[O:31])([OH:4])=[O:3].[C:32]([O:35][CH2:36]I)(=[O:34])[CH3:33].O>CN(C)C=O>[C:32]([O:35][CH2:36][O:3][C:2]([C:5]1[N:6]2[CH:9]([S:10][CH2:11][C:12]=1[CH2:13][S:14][C:15]1[N:19]([CH3:20])[N:18]=[N:17][N:16]=1)[CH:8]([NH:21][C:22](=[O:30])[CH2:23][C:24]1[S:25][C:26](=[O:29])[S:27][CH:28]=1)[C:7]2=[O:31])=[O:4])(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 5360545SodiumHCID 11820084Iodomethyl acetateHCID 214264602-Carboxy-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene

Product 1

HCID 214264782-Acetoxymethoxycarbonyl-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-eneYield 53.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

The sodium salt of 2-carboxy-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (5.08 g.) is dissolved in dimethylformamide (100 cc.) at 5° C. A solution of iodomethyl acetate (2 g.) in dimethylformamide (10 cc.) is added to this solution and the reaction mixture is stirred for 10 minutes at 5° C. It is then poured into water (500 cc.) and extracted twice with ethyl acetate (200 cc.). The combined organic phases are washed with water (100 cc.), saturated sodium bicarbonate solution (100 cc.), a 5% sodium bisulphite solution (100 cc.) and a saturated sodium chloride solution (100 cc.). The organic phase is dried over magnesium sulphate, filtered in the presence of decolourising charcoal and concentrated to dryness under reduced pressure (15 mm Hg). This gives a white product (5 g.) which is recrystallised from acetonitrile (50 cc.). 2-Acetoxymethoxycarbonyl-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (3 g.) is thus obtained as white crystals m.p. 154° C.

Workup

  1. extractionextracted twice with ethyl acetate (200 cc.)
  2. washThe combined organic phases are washed with water (100 cc.), saturated sodium bicarbonate solution (100 cc.)
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered in the presence of decolourising charcoal
  5. concentrationconcentrated to dryness under reduced pressure (15 mm Hg)
  6. customThis gives a white product (5 g.) which
  7. customis recrystallised from acetonitrile (50 cc.)

Sources & evidence

ORD record
ord-584b794bc89a436a87b0503b882a8328
Source dataset
uspto-grants-1977_07
Patent number
US04034090

Reaction notes

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