Pyridine-4-carbonyl chloride → 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-isonicotinoylthio-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester

HRID 1761389Notes

Reaction equation

HRID 1761389 reaction equation
[CH2:1]([O:4][C:5](=[O:41])[C:6]([N:26]1[C@H:29]([SH:30])[C@@H:28]([C@H:31]([O:33][C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])[CH3:32])[C:27]1=[O:40])=[P:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]=[CH2:3].[C:42](Cl)(=[O:49])[C:43]1[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=1>[Ag]>[CH2:1]([O:4][C:5](=[O:41])[C:6]([N:26]1[C@H:29]([S:30][C:42](=[O:49])[C:43]2[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=2)[C@@H:28]([C@H:31]([O:33][C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])[CH3:32])[C:27]1=[O:40])=[P:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 417436Pyridine-4-carbonyl chlorideHCID 140845622-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester

Product 1

HCID 572970702-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-isonicotinoylthio-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester

Reagents, catalysts & solvents 1

HCID 23954SilverCatalyst

Procedure

3.48 g of the silver salt of 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1yl]-2-triphenylphosphoranylideneacetic acid allyl ester are converted with isonicotinic acid chloride into the title compound analogously to Example 1.

Sources & evidence

ORD record
ord-47d21f93dc6b4b488492ba749498179c
Source dataset
uspto-grants-1989_05
Patent number
US04826832

Reaction notes

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