Water → HCID 88669831, compound

HRID 464223Notes

Reaction equation

HRID 464223 reaction equation
P(Br)(Br)[Br:2].[C:5]1([CH2:11][C:12]([NH:14][CH:15]2[C:40](=[O:41])[N:17]3[C:18]([C:24]([O:26][CH:27]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:25])=[C:19]([CH2:22]O)[CH2:20][S:21][C@H:16]23)=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O.[C:43]1([P:49]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>O1CCCC1.C(OCC)(=O)C>[Br-:2].[CH:27]([O:26][C:24]([C:18]1[N:17]2[C:40](=[O:41])[CH:15]([NH:14][C:12](=[O:13])[CH2:11][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[C@H:16]2[S:21][CH2:20][C:19]=1[CH2:22][P+:49]([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1)=[O:25])([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 24614Phosphorus tribromideHCID 13339796Benzhydryl 3-hydroxymethyl-7-phenylacetamido-3-cephem-4-carboxylate

Product 1

HCID 88669831HCID 88669831, compoundYield 147%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of phosphorus tribromide (5.0 g) in tetrahydrofuran (10 ml) was dropwise added to a mixture of benzhydryl 7-phenylacetamido-3-hydroxymethyl-3-cephem-4-carboxylate (25.7 g) in tetrahydrofuran (200 ml) at -10° to -5° C. and the mixture was stirred at the same temperature for 15 minutes. The resultant mixture was poured into a mixture of water (250 ml) and ethyl acetate (300 ml). The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated to give the oily product. The crude oily product was dissolved in ethyl acetate (250 ml) and triphenylphosphine (21 g) was added. The mixture was stirred at ambient temperature for 3 hours. The precipitate was collected by filtration and washed with ethyl acetate to give (4-benzhydryloxycarbonyl-7-phenylacetamido-3-cephem-3-ylmethyl)triphenyl phosphonium bromide (22.8 g).

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customto give the oily product
  5. stirringThe mixture was stirred at ambient temperature for 3 hours
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-d67a6e195cbf47698ad8d196778578af
Source dataset
uspto-grants-1985_10
Patent number
US04546101

Reaction notes

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