Phosphorus pentachloride → HCID 88521895, compound

HRID 1153924Notes

Reaction equation

HRID 1153924 reaction equation
[CH2:1]([O:3]/[N:4]=[C:5](/[C:9]1[N:10]=[C:11]([NH:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:12][CH:13]=1)\[C:6](O)=[O:7])[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:40][CH:41]1[C:66](=[O:67])[N:43]2[C:44]([C:50]([O:52][CH:53]([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)[C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[O:51])=[C:45]([CH2:48][Cl:49])[CH2:46][S:47][C@H:42]12.C([O-])(O)=O.[Na+]>ClCCl>[Cl:49][CH2:48][C:45]1[CH2:46][S:47][C@@H:42]2[CH:41]([NH:40][C:6](=[O:7])/[C:5](=[N:4]\[O:3][CH2:1][CH3:2])/[C:9]3[N:10]=[C:11]([NH:14][C:15]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[S:12][CH:13]=3)[C:66](=[O:67])[N:43]2[C:44]=1[C:50]([O:52][CH:53]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1)=[O:51]

Participants

6

Reactant 4

HCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 12784185HCID 12784185, compoundHCID 13239626Benzhydryl 7-Amino-3-chloromethyl-3-cephem-4-carboxylate

Product 1

HCID 88521895HCID 88521895, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (Z)-2-ethoxyimino-2-(2-tritylaminothiazol-4-yl)acetic acid (IV-2) (1.095 g, 2.4 mmoles) in dichloromethane (20 mL) was added phosphorous pentachloride (500 mg). After stirring for 1 hour at room temperature, the mixture was added in one portion to an ice-cooled solution of Compound V (1.083 g, 2.4 mmoles) and BSA (1 mL) in dichloromethane (20 mL). After stirring for 0.5 hour the reaction mixture was poured into 10% aqueous NaHCO3 (200 mL) and extracted with CHCl3 (100 mL). The extract was washed with water, dried over MgSO4, and evaporated under reduced pressure. The residue was chromatographed on a silica gel column. Elution with CHCl3 gave VI-2 as an amorphous powder, 1.76 g (86%).

Workup

  1. stirringAfter stirring for 0.5 hour the reaction mixture
  2. extractionextracted with CHCl3 (100 mL)
  3. washThe extract was washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed on a silica gel column
  7. washElution with CHCl3
  8. customgave VI-2 as an amorphous powder, 1.76 g (86%)

Sources & evidence

ORD record
ord-3685f297adaf4af588341334e1d0e745
Source dataset
uspto-grants-1984_12
Patent number
US04486586

Reaction notes

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