Hydrochloric Acid → HCID 70603825, compound

HRID 1390650Notes

Reaction equation

HRID 1390650 reaction equation
[CH:1]([C:3]1[CH:8]([C:9]([O:11][CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[N:7]2[C:25](=[O:36])[C@@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C@H:6]2[S:5][CH:4]=1)=[O:2].[CH:37]([Mg]Cl)=[CH2:38].P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>C(OCC)(=O)C.O.O1CCCC1>[OH:2][CH:1]([C:3]1[CH:8]([C:9]([O:11][CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[N:7]2[C:25](=[O:36])[C@@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C@H:6]2[S:5][CH:4]=1)[CH:37]=[CH2:38]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 24243Trisodium PhosphateHCID 62657Potassium Phosphate, TribasicHCID 88793624HCID 88793624, compoundHCID 178461836HCID 178461836, compound

Product 1

HCID 70603825HCID 70603825, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

This example illustrates step 1 of the first process described for preparing the compounds of the invention. In this example 2.5 g. of benzhydryl 3-formyl-7β-(thiophen-2-yl-acetamido)ceph-2-em-4-carboxylate in 50 ml. of anhydrous tetrahydrofuran is stirred under nitrogen at -70° C. and 10 ml. of 2.5 molar solution of vinyl magnesium chloride is added dropwise over five minutes. After 15 minutes, 50 ml. of a pH 7 buffer solution of dibasic sodium phosphate and monobasic potassium phosphate is added to the well stirred mixture which is then warmed to room temperature. The mixture is diluted with 200 ml. of water and layered with 200 ml. of ethyl acetate. The pH of the aqueous layer is adjusted to pH 4 by the addition of 20% aqueous hydrochloric acid. The ethyl acetate layer is separated and the aqueous layer extracted with 100 ml. ethyl acetate. The ethyl acetate extracts are combined and then washed twice with 50 ml. portions of brine, dried over sodium sulfate and evaporated under reduced pressure affording benzhydryl 3-(1-hydroxyprop-2-enyl)-7β-(thiophen-2-yl-acetamido)-ceph-2-em-4-carboxylate as a pale yellow oil (2.7 g.).

Workup

  1. customdescribed for preparing the compounds of the invention
  2. additionThe mixture is diluted with 200 ml
  3. customThe ethyl acetate layer is separated
  4. extractionthe aqueous layer extracted with 100 ml
  5. washwashed twice with 50 ml
  6. dry with materialportions of brine, dried over sodium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b66d11eea40d4649b08c405c1bd41618
Source dataset
uspto-grants-1979_02
Patent number
US04139618

Reaction notes

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