2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester → 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-[N-(4-allyloxycarbonylaminophenyl)-N-(allyloxycarbonyl)-glycylthio]2-oxo-azetidin-1-yl]-2-triphenylphosphoran-ylideneacetic acid allyl ester

HRID 1089131Notes

Reaction equation

HRID 1089131 reaction equation
C(O[C:5]1[CH:10]=[CH:9][C:8]([N:11]([C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17])[CH2:12][C:13]([OH:15])=O)=[C:7](N=C=O)[CH:6]=1)C=C.[CH2:25]([O:28][C:29](=[O:65])[C:30]([N:50]1[C@H:53]([SH:54])[C@@H:52]([C@H:55]([O:57][C:58]([O:60][CH2:61][CH:62]=[CH2:63])=[O:59])[CH3:56])[C:51]1=[O:64])=[P:31]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:26]=[CH2:27]>[Ag]>[CH2:25]([O:28][C:29](=[O:65])[C:30]([N:50]1[C@H:53]([S:54][C:13](=[O:15])[CH2:12][N:11]([C:8]2[CH:7]=[CH:6][C:5]([NH:11][C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17])=[CH:10][CH:9]=2)[C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17])[C@@H:52]([C@H:55]([O:57][C:58]([O:60][CH2:61][CH:62]=[CH2:63])=[O:59])[CH3:56])[C:51]1=[O:64])=[P:31]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:26]=[CH2:27]

Participants

4

Reactant 2

HCID 140845622-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl esterHCID 86744306N-(4-allyloxy-carbonylaminophenyl)-N-(allyloxycarbonyl)-glycine

Product 1

HCID 867443052-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-[N-(4-allyloxycarbonylaminophenyl)-N-(allyloxycarbonyl)-glycylthio]2-oxo-azetidin-1-yl]-2-triphenylphosphoran-ylideneacetic acid allyl ester

Reagents, catalysts & solvents 1

HCID 23954SilverCatalyst

Procedure

Analogously to Example 1, 2.67 g of N-(4-allyloxy-carbonylaminophenyl)-N-(allyloxycarbonyl)-glycine are converted with 3.5 g of the silver salt of 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester into the title compound.

Sources & evidence

ORD record
ord-08b186ab88d045d7a43eea7322596fd2
Source dataset
uspto-grants-1990_10
Patent number
US04965260

Reaction notes

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