1,5-Diazabicyclo(5,4,0)undec-5-ene → HCID 21772271, compound

HRID 1277709Notes

Reaction equation

HRID 1277709 reaction equation
[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:24])[C@H:12]2[C@@H:15](OS(OCC)(=O)=O)[CH3:16])[C:9]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:3])[CH3:2].N12CCCCC1C=NCCC2>ClCCl>[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:24])/[C:12]/2=[CH:15]/[CH3:16])[C:9]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:3])[CH3:2].[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:24])/[C:12]/2=[CH:15]\[CH3:16])[C:9]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 3141121,5-Diazabicyclo(5,4,0)undec-5-ene2×HCID 21772260HCID 21772260, compound

Product 2

HCID 21772271HCID 21772271, compoundHCID 21772272HCID 21772272, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Methyl (5R,6R)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-ethoxysulphonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (e22) (86 mg) was taken up in dichloromethane (3 ml) and treated with 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU) (33 mg) in dichloromethane (3.3 ml) added dropwise. After 15 minutes more DBU (3 mg) in dichloromethane (0.3 ml) was added and stirring was continued for 10 minutes. The solution was then washed with water (5 ml) and then chromatographed on silica gel to give methyl (5R,6E)-3-[(E)-2-acetamidoethenylthio]-6-ethylidene-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate and methyl (5R,6Z)-3-[(E)-2-acetamidoethenylthio]-6-ethylidene-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate as a mixture of isomers (e35 and e36) (21 mg), νmax (CH2Cl2) 1775 (broad), 1705, 1620 cm-1.

Workup

  1. additionadded dropwise
  2. washThe solution was then washed with water (5 ml)
  3. customchromatographed on silica gel

Sources & evidence

ORD record
ord-b0e75c3aa023489f86e027a88a5f011c
Source dataset
uspto-grants-1981_07
Patent number
US04278686

Reaction notes

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