Triphenylphosphine → HCID 88802658, compound

HRID 2419860Notes

Reaction equation

HRID 2419860 reaction equation
[I:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[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>[I-:1].[C:13]1([CH:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:11][C:9]([C: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][CH2:4][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 70615922HCID 70615922, compound

Product 1

HCID 88802658HCID 88802658, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of diphenylmethyl 3-iodomethyl-7β-(2-thienylacetamido)ceph-3-em-4-carboxylate (30 g.,) Rf 0.6 in ethyl acetate (500 ml.) was stirred in the dark at room temperature and treated, over 45 minutes, with a solution of triphenylphosphine (24.9 g., ca. 2 equivs.) in ethyl acetate (150 ml.). The mixture was stirred for a further 60 minutes at 0°, and the precipitated solid collected by filtration. The solid was washed with ethyl acetate and dried in vacuo to give the phosphonium iodide (31.7 g., 74.5%), Rf 0.0, m.p. 142°-146° (decomp.), [α]D + 10° (tetrahydrofuran), λmax 269 nm (ε 9,400) and 276 nm (ε 8,600) νmax (CHBr3) 3350 (NH), 1780 (β-lactam), 1710 (CO2R), 1680 and 1505 (CONH), and 1445 (P--C(aryl)) cm-1, τ (CDCl3) 4,39 (C(7) --H,dd,J 4.5 and 9 Hz), 5.19 (C(6) --H, d, J 4.5 Hz) 4.75 and 4.85 (CH2 --P, four major signals of two AB-q JP-H 16 Hz), 6.05 and 6.68 (C(2) -- CH2 two dd, JH-H 18 Hz, JP-H 3-4 Hz). [Found: C, 59.3; H, 4.5; I, 13.4; N, 2.6; P, 3.4; S, 7.3. C45H38IN2O4PS2 (892.8) requires C, 60.5; H, 4.3; I, 14.2; N, 3.1; P, 3.5; S, 7.2%].

Workup

  1. filtrationthe precipitated solid collected by filtration
  2. washThe solid was washed with ethyl acetate
  3. customdried in vacuo

Sources & evidence

ORD record
ord-ac60757de94542a7b80b1649db06bff2
Source dataset
uspto-grants-1978_08
Patent number
US04107431

Reaction notes

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