Hydrochloric Acid → HCID 70603825, compound

HRID 1763529Notes

Reaction equation

HRID 1763529 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

In this preparation 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 a 2.5 molar solution of vinyl magnesium-chloride is added dropwise over 5 minutes. After 15 minutes, 50 ml. of pH 7-buffer solution of dibasic sodium phosphate and monobasic potassium phosphate is added to the well stirred mixture, and 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. customIn this preparation 2.5 g
  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-7276e055bf164022b1ac0f1d6c64b1ac
Source dataset
uspto-grants-1978_09
Patent number
US04112087

Reaction notes

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