Tributylphosphine → HCID 70616310, compound

HRID 2420549Notes

Reaction equation

HRID 2420549 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].[CH2:37]([P:41]([CH2:46][CH2:47][CH2:48][CH3:49])[CH2:42][CH2:43][CH2:44][CH3:45])[CH2:38][CH2:39][CH3:40]>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+:41]([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:46][CH2:47][CH2:48][CH3:49])[CH2:37][CH2:38][CH2:39][CH3:40])=[O:10])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 13831TributylphosphineHCID 70615922HCID 70615922, compound

Product 1

HCID 70616310HCID 70616310, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of diphenylmethyl 3-iodomethyl-7β-(2-thienylacetamido)ceph-3-em-4-carboxylate (4.9 g.) in ethyl acetate (90 ml.) was stirred in the dark at room temperature and treated, over 15 minutes, with a solution of tri-n-butylphosphine (3.1 g., ca. 2 equivs.) in ethyl acetate (50 ml.). The solution was stirred for a further 45 minutes and precipitated into petroleum-ether to give the phosphonium iodide (3.448 g.), m.p. 120°-125° (decomp), [α]D - 43°(N,N-dimethylformamide), RF 0.0, inflexion (EtOH) at 259 nm. (ε 7,100), νmax. (CHBr3) 3410 (-NH), 1786 (β-lactam), 1708 (ester), and 1686 and 1510 cm. -1 (-CONH-), τ (CDCl3) 4.22 (C(7) -H, dd, J 5 and 9 Hz.), 4.87 (C(6) -H d, J 5 Hz), 5.80 and 6.11 (C(2) -CH2, two dd, JH-H 18 Hz., JP-H 3-4 Hz). [Found: C, 55.3; H, 6.0; I, 15.7; N, 3.1; P, 3.7 C39H50IN2O4PS2 (832.8) requires C, 56.2; H, 6.1; I, 15.1; N, 3.4; P, 3.7%].

Workup

  1. customprecipitated into petroleum-ether

Sources & evidence

ORD record
ord-967a3339a668414da438dff4cdfc89f8
Source dataset
uspto-grants-1978_08
Patent number
US04110534

Reaction notes

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