2-Dimethylaminopyridine → 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-(4-allyloxycarbonylaminophenoxyacetylthio)-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester

HRID 1089129Notes

Reaction equation

HRID 1089129 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][C:14]([OH:16])=O)=[CH:10][CH:9]=1)=[O:6])[CH:2]=[CH2:3].ClC(N(C)C)=C(C)C.[CH2:27]([O:30][C:31](=[O:67])[C:32]([N:52]1[C@H:55]([SH:56])[C@@H:54]([C@H:57]([O:59][C:60]([O:62][CH2:63][CH:64]=[CH2:65])=[O:61])[CH3:58])[C:53]1=[O:66])=[P:33]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:28]=[CH2:29].CN(C1C=CC=CN=1)C>C(Cl)Cl.[Ag].N1C=CC=CC=1>[CH2:27]([O:30][C:31](=[O:67])[C:32]([N:52]1[C@H:55]([S:56][C:14](=[O:16])[CH2:13][O:12][C:11]2[CH:10]=[CH:9][C:8]([NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])=[CH:18][CH:17]=2)[C@@H:54]([C@H:57]([O:59][C:60]([O:62][CH2:63][CH:64]=[CH2:65])=[O:61])[CH3:58])[C:53]1=[O:66])=[P:33]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:28]=[CH2:29]

Participants

8

Reactant 4

HCID 218852-DimethylaminopyridineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 140845622-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl esterHCID 221604452-(4-{[(Prop-2-en-1-yloxy)carbonyl]amino}phenoxy)acetic acid

Product 1

HCID 570957752-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-(4-allyloxycarbonylaminophenoxyacetylthio)-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester

Reagents, catalysts & solvents 3

HCID 23954SilverCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

1 g of 4-(allyloxycarbonylamino)-phenoxyacetic acid is suspended in 2 ml of CH2Cl2 and 0.6 ml of 1-chloro-1-dimethylamino-2-methylprop-1-ene is added thereto. The mixture is stirred for 75 minutes and is then added dropwise, over a period of 5 minutes, to a solution of 1.74 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, 50 mg of dimethylaminopyridine and 0.41 ml of pyridine in 30 ml of absolute methylene chloride. The title compound is obtained after working up analogously to Example 1.

Sources & evidence

ORD record
ord-1d8f7f00493542e1ba237657de13eb2b
Source dataset
uspto-grants-1990_10
Patent number
US04965260

Reaction notes

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