8-Hydroxyquinoline → HCID 131714653, compound

HRID 279771Notes

Reaction equation

HRID 279771 reaction equation
C([N+](CCCC)(CCCC)CCCC)CCC.[O:18]=[C:19]1[C@@H:22]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:21][N:20]1[S:34]([O-:37])(=[O:36])=[O:35].[OH:38][C:39]1[CH:40]=[CH:41][CH:42]=[C:43]2[C:48]=1[N:47]=[CH:46][CH:45]=[CH:44]2.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>ClC(Cl)C>[OH:38][C:39]1[CH:40]=[CH:41][CH:42]=[C:43]2[C:48]=1[NH+:47]=[CH:46][CH:45]=[CH:44]2.[O:18]=[C:19]1[C@@H:22]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:21][N:20]1[S:34]([O-:37])(=[O:35])=[O:36]

Participants

5

Reactant 3

HCID 19238-HydroxyquinolineHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 13575530tetrabutylammonium (S)-3-(((benzyloxy)carbonyl)amino)-2-oxoazetidine-1-sulfonate

Product 1

HCID 131714653HCID 131714653, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To a stirred solution of 3.58 g of (3S)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, tetrabutylammonium salt and 960 mg of 8-hydroxyquinoline in 10 ml of dichloroethane was added 1.53 g of camphorsulfonic acid. An additional 5 ml of dichloroethane was added and the mixture was stirred to effect solution and a seed crystal of the desired product was added to initiate precipitation. After ca. 5 minutes, 15 ml of ethyl acetate was added slowly. After an additional 30 minutes, the solid was isolated by filtration, washed with 1:1 dichloromethane/ethyl acetate and dried in vacuo to afford 1.98 g of the title compound as a fine, light yellow powder.

Sources & evidence

ORD record
ord-8d05e6ae18b4479a9d1ba99f5fa35884
Source dataset
uspto-grants-1986_05
Patent number
US04587051

Reaction notes

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