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

HRID 26583

Reaction equation

HRID 26583 reaction equation
C(=O)(O)[O-].[Na+].[C:6]([O:10][C:11]([C:13]1[N:14]2[CH:17]([S:18][CH2:19][C:20]=1[CH2:21][S:22][C:23]1[S:24][C:25]([CH3:28])=[N:26][N:27]=1)[CH:16]([NH2:29])[C:15]2=[O:30])=[O:12])([CH3:9])([CH3:8])[CH3:7].C1(N=C=NC2CCCCC2)CCCCC1.[N:46]1([CH2:51][C:52](O)=[O:53])[CH:50]=[CH:49][CH:48]=[CH:47]1.N=C=N>O1CCOCC1.O>[N:46]1([CH2:51][C:52]([NH:29][CH:16]2[C:15](=[O:30])[N:14]3[CH:17]2[S:18][CH2:19][C:20]([CH2:21][S:22][C:23]2[S:24][C:25]([CH3:28])=[N:26][N:27]=2)=[C:13]3[C:11]([O:10][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:12])=[O:53])[CH:50]=[CH:49][CH:48]=[CH:47]1

Participants

8

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 160435CarbodiimideHCID 2420271H-Pyrrol-1-ylacetic acidHCID 516892Sodium BicarbonateHCID 203279523-[[(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 tert-butyl ester

Product 1

HCID 867364847-[[(1-Pyrryl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

(1-Pyrryl)acetic (0.03m) 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 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 tert-butyl ester (0.1 m) (7-ATDCA) followed by N, N'-dicyclohexylcarbodiimide (0.01m) 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, and is recovered.

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. customis recovered

Sources & evidence

ORD record
ord-525e3a8a1a214c84a2c2210701a782a2
Source dataset
uspto-grants-1979_04
Patent number
US04150224

Linked notes

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