Potassium Carbonate → Benzoyl chloride

HRID 972738Notes

Reaction equation

HRID 972738 reaction equation
[CH2:1]1[C@@H:6](N)[C@H:5](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](N)[C@H]2O)[C@@H:4](O)[C@H:3](O[C@H]2O[C@H](CN)[C@@H](O)C[C@H]2N)[C@H:2]1N.[Cl:33][C:34](OC(=O)C1C=CC=CC=1)=[O:35].C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl.N1C=CC=CC=1>[C:34]([Cl:33])(=[O:35])[C:6]1[CH:5]=[CH:4][CH:3]=[CH:2][CH:1]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 36294TobramycinHCID 11735570Benzoyl chloroformate

Product 1

HCID 7412Benzoyl chloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

When the requisite 5-O-thioformyl intermediate is prepared by reacting tobramycin with an excess of benzoyl chloroformate and potassium carbonate in aqueous methanol in a manner similar to that described in Preparation 1A(1) followed by reaction of the thereby formed 1,3,2',6',3"-penta-N-benzyloxycarbonyltobramycin with benzoyl chloride in pryidine in the manner of Preparation 1C(1) thence reaction of the resulting 1,3,2',6',3"-penta-N-benzyloxycarbonyl-4',2",4",6"-tetra-O-benzoyltobramycin with N,N-dimethyl-α-chloroformimidinium chloride in methylene chloride in pyridine followed by treatment with dry hydrogen sulfide in a manner similar to that described in Preparation 1D(1) whereby is obtained 1,3,2',6',3"-penta-N-benzloxycarbonyl-5-O-thioformyl-4',2",4",6"-tetra-O-benzoyltobramycin.

Workup

  1. customWhen the requisite 5-O-thioformyl intermediate is prepared
  2. customthat described in Preparation
  3. customfollowed by reaction of the

Sources & evidence

ORD record
ord-0ced9176d47c4bbaafadc33cb1965992
Source dataset
uspto-grants-1977_10
Patent number
US04053591

Reaction notes

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