Ethyl Acetate → HCID 21426467, compound

HRID 258780Notes

Reaction equation

HRID 258780 reaction equation
[C:1]([O:7][CH2:8]I)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[K].[C:11]([C:14]1[N:15]2[CH:18]([S:19][CH2:20][C:21]=1[CH2:22][S:23][C:24]1[S:28][C:27]([CH3:29])=[N:26][N:25]=1)[CH:17]([NH:30][C:31](=[O:39])[CH2:32][C:33]1[S:34][C:35](=[O:38])[S:36][CH:37]=1)[C:16]2=[O:40])([OH:13])=[O:12].C(OCC)(=O)C>CN(C)C=O.O>[CH3:29][C:27]1[S:28][C:24]([S:23][CH2:22][C:21]2[CH2:20][S:19][CH:18]3[N:15]([C:16](=[O:40])[CH:17]3[NH:30][C:31](=[O:39])[CH2:32][C:33]3[S:34][C:35](=[O:38])[S:36][CH:37]=3)[C:14]=2[C:11]([O:13][CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[O:12])=[N:25][N:26]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 104401Iodomethyl pivalateHCID 5462222PotassiumHCID 21426458HCID 21426458, compound

Product 1

HCID 21426467HCID 21426467, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Iodomethyl pivalate (2.66 g.) is added to a suspension of the potassium salt of 2-carboxy-3-[(2-methyl-1,3,4-thiadiazol-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 (5.18 g.) in dimethyl formamide (100 cc.) cooled to 0° C. The reaction mixture is stirred for 10 minutes at 5° C.; it becomes limpid and is poured into a decanting funnel containing ethyl acetate (100 cc.) and water (200 cc.). The organic phase is washed with a saturated sodium bicarbonate solution (100 cc.) and then with a saturated sodium chloride solution (100 cc.). The organic phase is dried over sodium sulphate, treated with decolourising charcoal, filtered and concentrated to dryness under reduced pressure (20 mm Hg). The residue (5 g.) is chromatographed on silica (80 g.). A product (4.5 g.) is eluted with a 70-30 by volume mixture of ethyl acetate and cyclohexane, and is crystallised from a mixture of ethyl acetate and cyclohexane (50-50 by volume) (60 cc.). 3-[(2-Methyl-1,3,4-thiadiazol-5-yl)-thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-2-pivaloyloxymethoxycarbonyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (3 g.) is thus obtained as white crystals m.p. approximately 110° C.

Workup

  1. additionis poured into a decanting funnel
  2. washThe organic phase is washed with a saturated sodium bicarbonate solution (100 cc.)
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. additiontreated with decolourising charcoal
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (20 mm Hg)
  7. customThe residue (5 g.) is chromatographed on silica (80 g.)
  8. washA product (4.5 g.) is eluted with a 70-30 by volume mixture of ethyl acetate and cyclohexane
  9. customis crystallised from a mixture of ethyl acetate and cyclohexane (50-50 by volume) (60 cc.)

Sources & evidence

ORD record
ord-eee4f3dbadeb471290052db97371159d
Source dataset
uspto-grants-1977_07
Patent number
US04034090

Reaction notes

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