Phosphoric Acid → HCID 70504422, compound

HRID 1463140Notes

Reaction equation

HRID 1463140 reaction equation
S1C=CC=C1CC([NH:9][CH:10]1[C:42](=[O:43])[N:12]2[C:13]([C:26]([O:28][CH:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[C:14]([CH2:18][S:19][C:20]3[N:24]([CH3:25])[N:23]=[N:22][N:21]=3)[C@@H:15]([CH3:17])[S:16][C@H:11]12)=O.P(Cl)(Cl)(Cl)(Cl)Cl.OP([O-])([O-])=O.[K+].[K+].OP(O)(O)=O>C(Cl)Cl.CO.N1C=CC=CC=1>[NH2:9][CH:10]1[C:42](=[O:43])[N:12]2[C:13]([C:26]([O:28][CH:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[O:27])=[C:14]([CH2:18][S:19][C:20]3[N:24]([CH3:25])[N:23]=[N:22][N:21]=3)[C@@H:15]([CH3:17])[S:16][C@H:11]12

Participants

8

Reactant 4

HCID 1004Phosphoric AcidHCID 24450Potassium Phosphate, DibasicHCID 24819Phosphorus pentachlorideHCID 70505301HCID 70505301, compound

Product 1

HCID 70504422HCID 70504422, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A 3.7 ml portion of pyridine was added to a solution of diphenylmethyl 7-(2-thienylacetamido)-2α-methyl-3-(1-methyl-1H-tetrazol-5-yl)thiomethylceph-3-em-4-carboxylate in 100 ml of CH2Cl2, followed by adding 2.4 g of PCl5 at -12° C., further followed by stirring at the same temperature for 45 minutes. MeOH was added in once, and the mixture was further stirred at -10° C. for 30 minutes and at room temperature for 1 hour. 100 ml of 0.5M K2HPO4 solution was added to the reaction solution, followed by adding further 25% H3PO4 to adjust to pH 1.5. After stirring for 45 minutes, the CH2Cl2 layer was separated out, then washed with saturated aqueous NaCl solution, and dried over MgSO4 to distill off the CH2Cl2 under reduced pressure. Et2O was added to the residue, thus yielding 1.73 g (72%) of crystals of 7-amino-2α-methyl-3-(1-methyl-1H-tetrazol-5-yl)thiomethylceph-3-em-4-carboxylate.

Workup

  1. stirringwas further stirred at -10° C. for 30 minutes and at room temperature for 1 hour
  2. stirringAfter stirring for 45 minutes
  3. customthe CH2Cl2 layer was separated out
  4. washwashed with saturated aqueous NaCl solution
  5. dry with materialdried over MgSO4
  6. distillationto distill off the CH2Cl2 under reduced pressure
  7. additionEt2O was added to the residue

Sources & evidence

ORD record
ord-79402e024218492bab48e598e929cf47
Source dataset
uspto-grants-1984_07
Patent number
US04463172

Reaction notes

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