Water → Triphenylphosphine

HRID 1973662Notes

Reaction equation

HRID 1973662 reaction equation
C(C(C(=[P:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)CC1CS[C@@H]2[C@H](NC(=O)CC3SC=CC=3)C(=O)N2C=1C(OC(C)(C)C)=O)=O)C.O>O1CCCC1>[C:45]1([P:32]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

4

Reactant 2

HCID 962Water2×HCID 131710571HCID 131710571, compound

Product 1

HCID 11776TriphenylphosphineYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of t-butyl 3-(2-ethylcarbonyl-2-triphenylphosphoranylideneethyl)-7β-(2-thienylacetamido)ceph-3-em-4-carboxylate (500 mg.) in tetrahydrofuran (10 ml.) was treated with aluminum amalgam (500 mg., prepared as described in L.G. Fiester and M. Fieser, Reagents for Organic Synthesis, P. 20) and water (0.2 ml.), and the mixture stirred at 23°After 2 and 3 hours further amounts (0.2 ml., and 0.1 ml. respectively) of water were added. After a total of 4 hours the mixture was filtered and the filtrate evaporated in vacuo. The residue was dissolved in benzene and filtered through a short column of Merck Kieselgel (0.05 - 0.2mm, 10 g.) to give, on evaporation, triphenylphosphine (130 mg., 73%). Further elution with benzene ethyl acetate (1:1) gave the title compound (230 mg., 72%) as a foam, λmax. (EtOH) 270 nm (ε, 5,020), νmax. (CHBr3) 3450 and 3360 (NH), 1786 (β-lactam), 1730 (CO2R) and 1686 and 1518 cm-1 (CONH), τ(CDCl3) 3.51 (NH, doublet, J 9 Hz), 4.26 (C(7) -H, double doublet, J 9 and 4.5 Hz), 5.09 (C(6) -H, doublet, J 4.5 Hz), 5.88 and 8.74 (OCH2CH3, quartet and triplet), 6.17 (CH2CONH), 6.50 and 6.8 (C(2) -CH2, AB-quartet, J 18 Hz), 7.3-7.7 (--CH2CH2 --0--, 4 proton multiplet) and 8.47 (C[CH3]3).

Workup

  1. filtrationAfter a total of 4 hours the mixture was filtered
  2. customthe filtrate evaporated in vacuo
  3. dissolutionThe residue was dissolved in benzene
  4. filtrationfiltered through a short column of Merck Kieselgel (0.05 - 0.2mm, 10 g.)

Sources & evidence

ORD record
ord-7331ecfdb9414d369dfd18a8196ca3c9
Source dataset
uspto-grants-1976_12
Patent number
US03998821

Reaction notes

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