Triphenylphosphine → HCID 88802404, compound

HRID 1730886Notes

Reaction equation

HRID 1730886 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:37]([NH:38][C:39](=[O:47])[CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:36](=[O:48])[N:26]2[C:27]=1[C:28]([O:30][CH2:31][C:32]([Cl:35])([Cl:34])[Cl:33])=[O:29]>C(OCC)(=O)C>[Br-:20].[C:41]1([CH2:40][C:39]([NH:38][C@@H:37]2[C:36](=[O:48])[N:26]3[C:27]([C:28]([O:30][CH2:31][C:32]([Cl:33])([Cl:34])[Cl:35])=[O:29])=[C:22]([CH2:21][P+:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:23][S:24][C@H:25]23)=[O:47])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 70615562HCID 70615562, compound

Product 1

HCID 88802404HCID 88802404, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of triphenylphosphine (4.98 g, 2 equiv.) in ethyl acetate (30 ml) was added over a period of 15 minutes to a stirred solution of 2,2,2-trichloroethyl 3-bromomethyl-7β-phenylacetamidoceph-3-em-4-carboxylate (5.2 g, ca. 9.5 mmole) in ethyl acetate. The mixture was stirred in the absence of light for 2 hours when the precipitated solid was filtered off, washed with ethyl acetate and dried to give the title phosphonium salt (6.17 g, 81%), λmax. (EtOH) 268.5 nm (ε 10,450) and 275.5 nm (ε 10,050), νmax. (CHBr3) 3412 (NH), 1784 (azetidin-2-one), 1722 (CO2R), 1678 and 1498 (CONH) and 1440 cm-1 (P-+C6H5).

Workup

  1. filtrationwas filtered off
  2. washwashed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-1dd99c46ebd14e958cd3e04e2d4ecd04
Source dataset
uspto-grants-1976_11
Patent number
US03994884

Reaction notes

Loading…