Dicyclohexylcarbodiimide → HCID 86736753, compound

HRID 1448572Notes

Reaction equation

HRID 1448572 reaction equation
[CH:1]([C:3]1[N:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1)=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:27]([O:30][CH2:31][C:32]1[CH2:39][S:38][CH:37]2[N:34]([C:35](=[O:41])[CH:36]2[NH2:40])[C:33]=1[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])(=[O:29])[CH3:28]>O1CCCC1>[C:27]([O:30][CH2:31][C:32]1[CH2:39][S:38][CH:37]2[N:34]([C:35](=[O:41])[CH:36]2[NH:40][C:9](=[O:11])[CH2:8][N:4]2[CH:5]=[CH:6][CH:7]=[C:3]2[CH:1]=[O:2])[C:33]=1[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11771800HCID 11771800, compoundHCID 12459347(2-Formyl-1H-pyrrol-1-yl)acetic acid

Product 1

HCID 86736753HCID 86736753, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of (2-formyl-1-pyrryl)acetic acid (3.1 g, 0.02 m) in tetrahydrofuran (THF) is cooled to about 0° C. and 4.12 g (0.02 m) of dicyclohexylcarbodiimide is added in one portion with stirring for five minutes. Then 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, tert-butyl ester (6.08 g, 0.02 m) in THF is added. The temperature is maintained at 0° C. for one hour and then the temperature is increased to 20° for about 18 hours and the solution filtered. The THF is removed at reduced pressure and the residue is taken up in ethyl acetate. The ethyl acetate is extracted with 1.0% aqueous sodium bicarbonate and water. The ethyl acetate is then filtered, dried and evaporated to give the title compound.

Workup

  1. temperaturethe temperature is increased to 20° for about 18 hours
  2. filtrationthe solution filtered
  3. customThe THF is removed at reduced pressure
  4. extractionThe ethyl acetate is extracted with 1.0% aqueous sodium bicarbonate and water
  5. filtrationThe ethyl acetate is then filtered
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-fde6e25036964b97876725ebc73d7389
Source dataset
uspto-grants-1979_12
Patent number
US04180660

Reaction notes

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