Hydrochloric Acid → HCID 131712223, compound

HRID 2286633Notes

Reaction equation

HRID 2286633 reaction equation
C([NH:3][C:4]1[N:9]=[C:8]([C:10](=[N:42][O:43][CH3:44])[C:11]([NH:13][CH:14]2[C:40](=[O:41])[N:16]3[C:17]([C:37]([OH:39])=[O:38])=[C:18]([CH2:21][S:22][C:23]4[S:24][C:25]([CH2:28][NH:29]C(OC(C)(C)C)=O)=[N:26][N:27]=4)[CH2:19][S:20][C@H:15]23)=[O:12])[CH:7]=[CH:6][CH:5]=1)=O.CO.Cl>C(O)=O>[NH2:3][C:4]1[N:9]=[C:8]([C:10](=[N:42][O:43][CH3:44])[C:11]([NH:13][CH:14]2[C:40](=[O:41])[N:16]3[C:17]([C:37]([OH:39])=[O:38])=[C:18]([CH2:21][S:22][C:23]4[S:24][C:25]([CH2:28][NH2:29])=[N:26][N:27]=4)[CH2:19][S:20][C@H:15]23)=[O:12])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 131712224HCID 131712224, compound

Product 1

HCID 131712223HCID 131712223, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 7-[2-(6-formamidopyridin-2-yl)-2-methoxyiminoacetamido]-3-(5-t-butoxycarbonylaminomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(1.12 g.) in 98% formic acid (11 ml.) was stirred at room temperature for 2 hours. Methanol (20 ml.) and conc. hydrochloric acid (0.3 ml.) were added to the resultant solution and then stirred at room temperature for 30 minutes. After the reaction mixture was concentrated in vacuo, water (25 ml.) was added to the residue, and then the solution was adjusted to pH 3 to 4 with a saturated aqueous solution of sodium bicarbonate. The solution was subjected to column chromatography on macroporous, non-ionic adsorption resin "Diaion HP-20" (Trademark, manufactured by Mitsubishi Chemical Industries Ltd.) with an eluent of aqueous methanol. The eluate was concentrated under reduced pressure and lyophilized to give 7-[2-(6-aminopyridin-2-yl)-2-methoxyiminoacetamido]-3-(5-aminomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.48 g.), mp. 248° to 251° C. (dec.).

Workup

  1. concentrationAfter the reaction mixture was concentrated in vacuo, water (25 ml.)
  2. additionwas added to the residue
  3. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-57ef3b60f4094b02ac005efab247db99
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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