Triphenylphosphine → HCID 88802324, compound

HRID 2419865Notes

Reaction equation

HRID 2419865 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][C:22]1[CH2:23][S:24][C@@H:25]2[C@H:36]([NH:37][C:38](=[O:47])[CH2:39][O:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:35](=[O:48])[N:26]2[C:27]=1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>C(OCC)(=O)C>[Br-:20].[C:31]([O:30][C:28]([C:27]1[N:26]2[C:35](=[O:48])[C@@H:36]([NH:37][C:38](=[O:47])[CH2:39][O:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C@H:25]2[S:24][CH2:23][C:22]=1[CH2:21][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 70615395HCID 70615395, compound

Product 1

HCID 88802324HCID 88802324, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of triphenylphosphine (1.95 g, 2 equiv.) in ethyl acetate (6 ml) was added to a solution of t-butyl 3-bromomethyl-7β-phenoxyacetamidoceph-3-em-4-carboxylate (1.80 g, 3.72 mmole) in ethyl acetate (4 ml.). The mixture was stirred for 1 hour, and the precipitated solid was filtered off, washed with ether and dried to give the title phosphonium salt (2.42 g, 87.5%), m.p. 144° to 146°,[α]D22 +31° (C 0.95; Me2SO), λmax. (EtOH) 268 nm (ε 11,300) and 275 nm (ε 10,400), νmax. (Nujol) 3400 (NH), 1778 (azetidin-2-one), 1692 and 1520 (CONH), 1690 (CO2R) and 1430 cm-1 (P+ -C6H5), τ (Me2SO-d6) 0.89 (1H,d, j 8 Hz; NH), 2.66 and 2.99 (2H and 3H, 2 m; C6H5O), 4.29 (1H, centres of two AB-quartets, JH-H 15 Hz, JP-H 16 Hz; C3 -CH2P+), 5.33 (2H,s; C6H5OCH2), 8.76 (9H, s; CO2C(CH3)3).

Workup

  1. filtrationthe precipitated solid was filtered off
  2. washwashed with ether
  3. customdried

Sources & evidence

ORD record
ord-3e98182a69a9465baaddd5cd97c7ef11
Source dataset
uspto-grants-1978_08
Patent number
US04107431

Reaction notes

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