Diisopropyl Ether → HCID 131714487, compound

HRID 1284581Notes

Reaction equation

HRID 1284581 reaction equation
[CH2:1]([O:4][N:5]=[C:6]([C:29]1[N:33]=[C:32]([NH:34][P:35]([O:39]C)([O:37]C)=[O:36])[S:31][N:30]=1)[C:7]([NH:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:24]([O-:26])=[O:25])=[C:14]([CH2:17][N+:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[CH:2]=[CH2:3].C(ON=C(C1N=C(NP(OC)(OC)=O)SN=1)C([O-])=O)C=C.[Na+].Cl.Cl.NC1C(=O)N2C(C([O-])=O)=C(C[N+]3C=CC=CC=3)CS[C@H]12.C[Si](Br)(C)C.C(OC(C)C)(C)C>C(O)(=O)C>[CH2:1]([O:4][N:5]=[C:6]([C:29]1[N:33]=[C:32]([NH:34][P:35]([OH:37])([OH:39])=[O:36])[S:31][N:30]=1)[C:7]([NH:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:24]([O-:26])=[O:25])=[C:14]([CH2:17][N+:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[CH:2]=[CH2:3]

Participants

7

Reactant 5

HCID 7914Diisopropyl EtherHCID 76113BromotrimethylsilaneHCID 67897138HCID 67897138, compoundHCID 74088770HCID 74088770, compoundHCID 131714485HCID 131714485, compound

Product 1

HCID 131714487HCID 131714487, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 7-[2allyloxyimino-2-{5-dimethoxyphosphorylamino-1,2,4-thiadiazol-3-yl}acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) in the reaction mixture prepared from sodium 2allyloxyimino-2-[5-dimethoxyphosphorylamino-1,2,4-thiadiazol-3-yl]acetate (syn isomer) (502 mg) and 7-amino-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate dihydrochloride (560 mg) according to a similar procedure to that of Example 1 was added dropwise trimethylsilyl bromide (3.22 g) under cooling in an ice bath and stirring, which was continued for one hour at room temperature. To the mixture was added acetic acid (0.5 ml) and the mixture was poured into diisopropyl ether (500 ml) under stirring. The resulting oily product was separated out by decantation and dissolved in water (50 ml). The aqueous solution was subjected to column chromatography on a non ionic adsorption resin "Diaion HP-20" (50 ml). The elution was carried out with water and 10% aqueous methanol. The fractions containing the object compound were collected, evaporated to remove methanol under reduced pressure and lyophilized to give 7-[2-allyloxyimino-2-(5-phosphonoamino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (250 mg), mp. 175° to 181° C. (dec.).

Workup

  1. temperatureunder cooling in an ice bath
  2. stirringunder stirring
  3. customThe resulting oily product was separated out by decantation
  4. dissolutiondissolved in water (50 ml)
  5. washThe elution
  6. additionThe fractions containing the object compound
  7. customwere collected
  8. customevaporated
  9. customto remove methanol under reduced pressure

Sources & evidence

ORD record
ord-e7ad946ccba74f4b97501d8553fc6984
Source dataset
uspto-grants-1986_01
Patent number
US04563449

Reaction notes

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