Triphenylphosphine → HCID 88802291, compound

HRID 2420554Notes

Reaction equation

HRID 2420554 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][CH:39]=[O:40])[C:36](=[O:41])[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].[CH:39]([NH:38][C@@H:37]1[C:36](=[O:41])[N:26]2[C:27]([C:28]([O:30][CH2:31][C:32]([Cl:34])([Cl:33])[Cl:35])=[O:29])=[C:22]([CH2:21][P+:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:23][S:24][C@H:25]12)=[O:40]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 88801790HCID 88801790, compound

Product 1

HCID 88802291HCID 88802291, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of triphenylphosphine (1.06 g, 2 equiv.) in ethyl acetate (5 ml) was added to a stirred solution of 2,2,2-trichloroethyl 3-bromomethyl-7β-formamidoceph-3-em-4-carboxylate (0.91 g, 2 mmole) in ethyl acetate (5 ml). The mixture was stirred at ca. 20° for 45 minutes and then warmed to 45° for 10 minutes. The precipitated solid was filtered off, washed with ethyl acetate and ether, and dried to give the title phosphonium salt (1.06 g, 74%), m.p. 151° to 153° (dec.), [α]D + 92° (C 1.0; CHCl3), λmax. (EtOH) 268.5 nm (ε 9,000) and 275 nm (ε 9,000), νmax. (CHBr3) 3430 (NH), 1795 (azetidin-2-one), 1730 (CO2R), 1700 (CONH) and 1445 cm-1 (P+ -C6H5), 0.91 (1H,d, J9 Hz; NH), 4.25 (1H,dd, J 9 and 5 hz; C7 -H), 4.67 (1H,d, J 5 Hz; C6 -H), 4.77 and 4.93 (2H, centers of two collapsed AB-quarters, JP-H 16 Hz; C3 -CH2P+), 5.25 and 5.45 (2H, AB-q, J 12 Hz; CH2CCl3) (Found: C, 46.9; H, 3.7; N, 3.7; P, 3.7; S, 3.9%; total halogen content, 3.9 equiv./mole compound. C29H25BrCl3N2O4PS (714.9) requires C, 48.7; H, 3.5; N, 3.9; P, 4.3; S, 4.5%; total halogen content 4 equiv./mole compound).

Workup

  1. temperaturewarmed to 45° for 10 minutes
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with ethyl acetate and ether
  4. customdried

Sources & evidence

ORD record
ord-2fdc3d443bb947f3b4d0edbf186941d6
Source dataset
uspto-grants-1978_08
Patent number
US04110534

Reaction notes

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