Water → HCID 131715056, compound

HRID 236217Notes

Reaction equation

HRID 236217 reaction equation
[SH:1][C:2]1[N:6]([CH3:7])[N:5]=[N:4][N:3]=1.P1(Cl)(=O)OC2C=CC=CC=2O1.[C:19]1([CH:25]([C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)[O:26][C:27]([CH:29]([N:63]2[C:67](=[O:68])[C:66]3=[CH:69][CH:70]=[CH:71][CH:72]=[C:65]3[C:64]2=[O:73])[CH2:30][CH2:31][CH2:32][C:33]([NH:35][C@@H:36]2[C:61](=[O:62])[N:38]3[C:39]([C:45]([O:47][CH:48]([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)[C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)=[O:46])=[C:40]([CH2:43]O)[CH2:41][S:42][C@H:37]23)=[O:34])=[O:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C(Cl)Cl>[C:19]1([CH:25]([C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)[O:26][C:27]([CH:29]([N:63]2[C:67](=[O:68])[C:66]3=[CH:69][CH:70]=[CH:71][CH:72]=[C:65]3[C:64]2=[O:73])[CH2:30][CH2:31][CH2:32][C:33]([NH:35][C@@H:36]2[C:61](=[O:62])[N:38]3[C:39]([C:45]([O:47][CH:48]([C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)[C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)=[O:46])=[C:40]([CH2:43][S:1][C:2]4[N:6]([CH3:7])[N:5]=[N:4][N:3]=4)[CH2:41][S:42][C@H:37]23)=[O:34])=[O:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 739091,3,2-Benzodioxaphosphole, 2-chloro-, 2-oxideHCID 70505128HCID 70505128, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 131715056HCID 131715056, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-10 °C

Procedure

In 5 ml of methylene chloride was dissolved 0.195 g of 5-mercapto-1-methyl-1H-tetrazole and the solution was cooled to -10° C. Then, a solution of 0.268 g of o-phenylene phosphorochloridate in 5 ml of methylene chloride was added and, under cooling at -20° to -25° C., a solution of 1.170 g of diphenylmethyl 7β-(5-diphenylmethyloxycarbonyl-5-phthalimidovaleramido)-3-hydroxymethyl-3-cephem-4-carboxylate in 8 ml of methylene chloride was added dropwise. The mixture was stirred at the same temperature for 20 minutes. To the reaction mixture was added 10 ml of water and, then, the mixture was allowed to stand at room temperature for phase separation. The organic layer was washed with water, dried over anhydrous sodium sulfate, concentrated and poured into 80 ml of ether. The powdery precipitate was collected by filtration and subjected to silica gel column chromatography (silica gel: 30 g, column height: 36 cm), elution being carried out with ethyl acetate-n-hexane (4:1). The fractions were checked by TLC (developing solvent: the same as the above eluent) and the fractions (Rf : about 0.71) containing the desired product were collected and concentrated. To the concentrate was added ether to give diphenylmethyl 7β-(5-diphenylmethyloxycarbonyl-5-phthalimidovaleramido)-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylate.

Workup

  1. temperatureunder cooling at -20° to -25° C.
  2. customto stand at room temperature for phase separation
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionpoured into 80 ml of ether
  7. filtrationThe powdery precipitate was collected by filtration
  8. washsubjected to silica gel column chromatography (silica gel: 30 g, column height: 36 cm), elution
  9. additionthe same as the above eluent) and the fractions (Rf : about 0.71) containing the desired product
  10. customwere collected
  11. concentrationconcentrated
  12. additionTo the concentrate was added ether

Sources & evidence

ORD record
ord-33e72321efc9476c888c2cbf69783ce6
Source dataset
uspto-grants-1987_02
Patent number
US04642365

Reaction notes

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