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

HRID 1089127Notes

Reaction equation

HRID 1089127 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].N1C=CC=CC=1.[F:48][C:49]1[CH:59]=[CH:58][C:52]([O:53][CH2:54][C:55](Cl)=[O:56])=[CH:51][CH:50]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1.[Ag]>[CH2:1]([O:4][C:5](=[O:41])[C:6]([N:26]1[C@H:29]([S:30][C:55](=[O:56])[CH2:54][O:53][C:52]2[CH:58]=[CH:59][C:49]([F:48])=[CH:50][CH:51]=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

7

Reactant 3

HCID 1049PyridineHCID 2759057(4-Fluorophenoxy)acetyl chlorideHCID 140845622-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester

Product 1

HCID 570084032-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-(4-fluorophenoxyacetylthio)-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23954SilverCatalystHCID 6344DichloromethaneSolvent

Procedure

1.74 g of the silver salt of 2-[(3S,4R)-3-[(1R)-1allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester are reacted in 30 ml of methylene chloride with 0.41 ml of pyridine, 20 mg of 4-dimethylaminopyridine and 0.7 g of 4-fluorophenoxyacetyl chloride. After working up analogously to Example 1, 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-(4-fluorophenoxyacetylthio)-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester is obtained.

Sources & evidence

ORD record
ord-02cd9cc85a9d4c07983f251ea42542c1
Source dataset
uspto-grants-1990_10
Patent number
US04965260

Reaction notes

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