4-Toluenesulfonyl chloride → 1,5-Diazabicyclo(4.3.0)non-5-ene

HRID 1457965Notes

Reaction equation

HRID 1457965 reaction equation
CS(Cl)(=O)=O.[C:6]1([CH3:16])[CH:11]=[CH:10][C:9](S(Cl)(=O)=O)=[CH:8]C=1.[CH2:17]([N:19]([CH2:22][CH3:23])CC)C.[N:24]1[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=1C>N1C=CC=CC=1>[N:19]12[CH2:22][CH2:23][CH2:25][N:24]=[C:16]1[CH2:6][CH2:11][CH2:10][CH2:9][CH2:8]2.[N:24]12[CH2:28][CH2:27][CH2:26][C:25]1=[N:19][CH2:17][CH2:30][CH2:29]2

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 79372,6-LutidineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 2

HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

This compound is converted into sulfonate by allowing it to react with methanesulfonyl chloride or p-toluenesulfonyl chloride using triethylamine, pyridine or the like base as an acid-removing agent, and the resulting compound is then allowed to react with pyridine, 2,6-lutidine or the like aromatic heterocyclic compound or 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene or the like organic base to give ethyl 1-tert-butoxycarbonylaminocyclobutanepropenoate.

Sources & evidence

ORD record
ord-9428948651b340cf9b97831b0e57e9e8
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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