Triphenylphosphine → HCID 88802302, compound

HRID 2420556Notes

Reaction equation

HRID 2420556 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:45]([NH:46][C:47](=[O:56])[CH2:48][O:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:44](=[O:57])[N:26]2[C:27]=1[C:28]([O:30][CH:31]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>C(OCC)(=O)C>[Br-:20].[C:38]1([CH:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[O:30][C:28]([C:27]2[N:26]3[C:44](=[O:57])[C@@H:45]([NH:46][C:47](=[O:56])[CH2:48][O:49][C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=4)[C@H:25]3[S:24][CH2:23][C:22]=2[CH2:21][P+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:29])[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 22806612HCID 22806612, compound

Product 1

HCID 88802302HCID 88802302, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of triphenylphosphine (0.99 g, 1.5 equiv.) in ethyl acetate (10 ml) was added to a stirred solution of diphenylmethyl 3-bromomethyl-7β-phenoxyacetamidoceph-3-em-4-carboxylate (ca. 1.49 g, 2.515 mmole) in ethyl acetate (25 ml). The mixture was stirred in the absence of light for 16 hours, and the precipitated solid was filtered off, washed with ethyl acetate and dried to give the title phosphonium salt (1.585 g, 74%), λmax. (EtoH) 268.5 nm (ε 10,700) and 275.5 nm(ε 9,850), νmax. (CHBr3), 3415 (NH), 1788 (azetidin-2-one), 1710 (CO2R), 1692 and 1620 (CONH) and 1440 cm-1 (P+ -C6H5).

Workup

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

Sources & evidence

ORD record
ord-7dbd22bd888b432eb97d258498e54adc
Source dataset
uspto-grants-1978_08
Patent number
US04110534

Reaction notes

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