Triphenylphosphine → HCID 131710535, compound

HRID 1730883Notes

Reaction equation

HRID 1730883 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]([C:9]([O:11][CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[N:7]2[C:25](=[O:36])[C@@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C@H:6]2[S:5][CH:4]=1.[C:37]1([P:43]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(OCC)(=O)C>[Cl-:1].[C:13]1([CH:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:11][C:9]([CH:8]2[N:7]3[C:25](=[O:36])[C@@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]4[S:31][CH:32]=[CH:33][CH:34]=4)[C@H:6]3[S:5][CH:4]=[C:3]2[CH2:2][P+:43]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:10])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 69010900HCID 69010900, compound

Product 1

HCID 131710535HCID 131710535, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of diphenylmethyl 3-chloromethyl-7β-(2-thienylacetamido)ceph-2-em-4-carboxylate (2.3 g.) in ethyl acetate (20 ml.) was treated with triphenylphosphine (2.3 g., ca. 2 equivs.) and the mixture refluxed for 5 hours. The solution was cooled and the insoluble product isolated by filtration. This material was precipitated from acetone (containing some chloroform) solution by petroleum-ether to give the phosphonium salt (500 mg.) as an amorphous solid [α]D + 68.5° (CHCl3), λmax. (CHCl3) 269.5 and 276.5 nm. (ε 8,880 and 7,620), νmax. (CHBr3) 3440 (NH), 1780 (β-lactam), 1680 and 1510 (--CONH--), and 1445 (P-C aryl) cm,-1, τ(CDCl3) 3.61 (C(2) -H), 4.4 (C(7) -H, dd, J 4.5 and 9 Hz), 4.75 (C(6) -H, not well resolved), 5.04 and 5.18 (CH2 -P, part of two AB-q, JP-H 13 Hz.).

Workup

  1. temperaturethe mixture refluxed for 5 hours
  2. temperatureThe solution was cooled
  3. customthe insoluble product isolated by filtration
  4. customThis material was precipitated from acetone (
  5. additioncontaining some chloroform) solution by petroleum-ether

Sources & evidence

ORD record
ord-4725b15e79214171b06d2f233ff052f8
Source dataset
uspto-grants-1976_11
Patent number
US03994884

Reaction notes

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