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Water → HCID 88669831, compound

HRID 980994
Notes
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Reaction equation

HRID 980994 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028
Tetrahydrofuran
Solvent
2×
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-a0d67c20908a48fdab88ba4083736375
Source dataset
uspto-grants-1987_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04639448

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes