Pyridine → 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-[5-(tetrazol-1-yl)-pentanoylthio]-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester

HRID 414751Notes

Reaction equation

HRID 414751 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.[N:48]1([CH2:53][CH2:54][CH2:55][CH2:56][C:57](Cl)=[O:58])[CH:52]=[N:51][N:50]=[N:49]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:57](=[O:58])[CH2:56][CH2:55][CH2:54][CH2:53][N:48]2[CH:52]=[N:51][N:50]=[N:49]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 140845622-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl esterHCID 178034065-(Tetrazol-1-yl)-valeric acid chloride

Product 1

HCID 571673172-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-[5-(tetrazol-1-yl)-pentanoylthio]-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23954SilverCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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 are dissolved in 30 ml of methylene chloride, and, at 0°, 0.41 ml of pyridine, 50 mg of 4-dimethylaminopyridine and then, dropwise, a solution of 0.87 g of 5-(tetrazol-1-yl)-valeric acid chloride in 15 ml of methylene chloride are added. After stirring for 30 minutes at 0°, the solid material is filtered off over Hyflo and the filtrate is washed with aqueous sodium bicarbonate solution and then with brine. After drying over MgSO4, the solution is concentrated by evaporation. The residue is purified by chromatography over silica gel (eluant toluene/ethyl acetate: 9:1 to 1:1). TLC (ethyl acetate) Rf =0.33; IR (CH2Cl2): 1750, 1690, 1620 cm-1.

Workup

  1. filtrationthe solid material is filtered off over Hyflo
  2. washthe filtrate is washed with aqueous sodium bicarbonate solution
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe solution is concentrated by evaporation
  5. customThe residue is purified by chromatography over silica gel (eluant toluene/ethyl acetate: 9:1 to 1:1)

Sources & evidence

ORD record
ord-944b9315c8d148288c1200bf6f440897
Source dataset
uspto-grants-1988_12
Patent number
US04794109

Reaction notes

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