Tetrahydrofuran → HCID 88716201, compound

HRID 543558Notes

Reaction equation

HRID 543558 reaction equation
[C:1]([CH2:4][C@H:5]1[N:8]([C:9]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])=[P:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7](=[O:39])[C@H:6]1[CH:40]([O:42][C:43](=[O:45])[CH3:44])[CH3:41])(O)=O.C(N([CH2:51][CH3:52])CC)C.C(OP(Cl)(=O)OCC)C.C1C=CC([S-:68])=CC=1.[Na+].O1[CH2:74][CH2:73][CH2:72][CH2:71]1>>[C:52]1([C:1]([CH2:4][C@H:5]2[N:8]([C:9]([C:29]([O:31][CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:30])=[P:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:7](=[O:39])[C@H:6]2[CH:40]([O:42][C:43](=[O:45])[CH3:44])[CH3:41])=[S:68])[CH:51]=[CH:74][CH:73]=[CH:72][CH:71]=1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran4×HCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 4110039Sodium benzenethiolateHCID 86739393HCID 86739393, compound

Product 1

HCID 88716201HCID 88716201, compound

Procedure

Cis-4-carboxymethyl-3-(1-acetoxyethyl)-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one (0.61 g) in dry tetrahydrofuran (50 cm3) was treated with triethylamine (0.12 g) in dry tetrahydrofuran (1 cm3), and the solution was cooled to 0° under argon. Diethylphosphorochloridate (0.2 g) in dry tetrahydrofuran (20 cm3) was added dropwise, and the solution was stirred for three hours at room temperature under argon. The solution was treated with sodium phenylthiolate (0.13 g) in dry tetrahydrofuran (10 cm3), and the mixture was stirred at room temperature for one hour. Filtration and evaporation under reduced pressure gave a residue which was chromatographed on silica gel 60 (<230 mesh) eluting with a 1:1 ethyl acetate/60°-80° petroleum ether mixture. This gave cis-4-phenylthiocarbonylmethyl-3-(1-acetoxyethyl)-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one (0.30 g, 43%); νmax (CHCl3) 3000, 1735, 1690 and 1610 cm- 1.

Workup

  1. temperaturethe solution was cooled to 0° under argon
  2. stirringthe mixture was stirred at room temperature for one hour
  3. filtrationFiltration and evaporation under reduced pressure
  4. customgave a residue which
  5. customwas chromatographed on silica gel 60 (<230 mesh)
  6. washeluting with a 1:1 ethyl acetate/60°-80° petroleum ether mixture

Sources & evidence

ORD record
ord-bae55a0dfa144bb188aefcaaca95d6e1
Source dataset
uspto-grants-1984_05
Patent number
US04446146

Reaction notes

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