Dicyclohexylcarbodiimide → 7-[[(1-Pyrryl)acetyl]amino]-3-[[(5-methyl-1,3,4-thia-diazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 26581

Reaction equation

HRID 26581 reaction equation
C(=O)(O)[O-].[Na+].[CH3:6][C:7]1[S:11][C:10]([S:12][CH2:13][C:14]2[CH2:21][S:20][CH:19]3[N:16]([C:17](=[O:23])[CH:18]3[NH2:22])[C:15]=2[C:24]([OH:26])=[O:25])=[N:9][N:8]=1.C1(N=C=NC2CCCCC2)CCCCC1.[N:42]1([CH2:47][C:48](O)=[O:49])[CH:46]=[CH:45][CH:44]=[CH:43]1.N=C=N>O1CCOCC1.O>[N:42]1([CH2:47][C:48]([NH:22][CH:18]2[C:17](=[O:23])[N:16]3[CH:19]2[S:20][CH2:21][C:14]([CH2:13][S:12][C:10]2[S:11][C:7]([CH3:6])=[N:8][N:9]=2)=[C:15]3[C:24]([OH:26])=[O:25])=[O:49])[CH:46]=[CH:45][CH:44]=[CH:43]1

Participants

8

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 160435CarbodiimideHCID 2420271H-Pyrrol-1-ylacetic acidHCID 516892Sodium BicarbonateHCID 31498227-Amino-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 572026407-[[(1-Pyrryl)acetyl]amino]-3-[[(5-methyl-1,3,4-thia-diazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

(1-Pyrryl)acetic is added to water, the pH of which is adjusted to about 6.5 by the addition of sodium bicarbonate. This solution is cooled in an ice bath and to it is added one equivalent of 3-[[(5 methyl - 1, 3, 4-thiadiazol-2-yl) thio]methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (7-ATDCA) followed by N, N'-dicyclohexylcarbodiimide in cold dioxane. The mole ratio of (1-pyrryl) acetic acid/7-ATDCA/carbodiimide is 3/1/1. After standing overnight at ice bath temperature, the reaction mixture is filtered to remove solids. The filtrate is evaporated to dryness, the solids taken up in ethyl acetate, dried over magnesium sulfate and filtered. The ethyl acetate solution is concentrated and then treated with hexane. The title compound precipitates from solution is filtered and dried. EXAMPLE 6

Workup

  1. temperatureThis solution is cooled in an ice bath and to it
  2. filtrationtemperature, the reaction mixture is filtered
  3. customto remove solids
  4. customThe filtrate is evaporated to dryness
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe ethyl acetate solution is concentrated
  8. additiontreated with hexane
  9. customThe title compound precipitates from solution
  10. filtrationis filtered
  11. customdried

Sources & evidence

ORD record
ord-bbc0e2fe771e45e4926192ad2c649d57
Source dataset
uspto-grants-1979_04
Patent number
US04150224

Linked notes

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