Phosphorus pentachloride → HCID 88521895, compound

HRID 1462037Notes

Reaction equation

HRID 1462037 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 (IVb) (1.095 g, 2.4 mmoles) in dichloromethane (20 mL) was added phosphorus 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 VIb 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 VIb as an amorphous powder, 1.76 g (86%)

Sources & evidence

ORD record
ord-4711297247d74f30bc464f260dcf8082
Source dataset
uspto-grants-1984_07
Patent number
US04457929

Reaction notes

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