HCID 131712400, compound → HCID 131712399, compound

HRID 648398Notes

Reaction equation

HRID 648398 reaction equation
C(OC([NH:9][C:10]1[S:11][CH:12]=[C:13]([C:15](=[O:42])[C:16]([NH:18][CH:19]2[C:40](=[O:41])[N:21]3[C:22]([C:37]([OH:39])=[O:38])=[C:23]([CH2:26][S:27][C:28]4[N:32]([CH2:33][C:34]([OH:36])=[O:35])[N:31]=[N:30][N:29]=4)[CH2:24][S:25][C@H:20]23)=[O:17])[N:14]=1)=O)(CC)(C)C>C(O)=O>[NH2:9][C:10]1[S:11][CH:12]=[C:13]([C:15](=[O:42])[C:16]([NH:18][CH:19]2[C:40](=[O:41])[N:21]3[C:22]([C:37]([OH:39])=[O:38])=[C:23]([CH2:26][S:27][C:28]4[N:32]([CH2:33][C:34]([OH:36])=[O:35])[N:31]=[N:30][N:29]=4)[CH2:24][S:25][C@H:20]23)=[O:17])[N:14]=1

Participants

3

Reactant 1

HCID 131712400HCID 131712400, compound

Product 1

HCID 131712399HCID 131712399, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 7-[2-(2-tert-pentyloxycarbonylamino-1,3-thiazol-4-yl)glyoxylamido]-3-(1-carboxymethyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (870 mg.) and 99% formic acid (16 ml.) was stirred for 3.5 hours at ambient temperature. The solvent was distilled off and to the residue was added diethyl ether (20 ml.). Insoluble material was collected by filtration and dissolved in 5% sodium bicarbonate aqueous solution (20 ml.) the aqueous solution was washed with ethyl acetate (20 ml.) and to the resulting aqueous solution was added ethyl acetate (60 ml.). The mixture was adjusted to pH 2.0 and 10% hydrochloric acid with stirring to precipitate powder. The precipitates were collected by filtration, well stirred in ethyl acetate (50 ml.) to remove impurities and collected by filtration to give 7-[2-(2-amino-1,3-thiazol-4-yl)glyoxylamido]-3-(1-carboxymethyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (240 mg.). The aqueous layer in the filtrate of pH 2.0 as mentioned above was separated and allowed to stand overnight. Precipitates were collected by filtration further to give the same object compound (120 mg.). Total yield 360 mg.

Workup

  1. distillationThe solvent was distilled off and to the residue
  2. additionwas added diethyl ether (20 ml.)
  3. filtrationInsoluble material was collected by filtration
  4. dissolutiondissolved in 5% sodium bicarbonate aqueous solution (20 ml.) the aqueous solution
  5. washwas washed with ethyl acetate (20 ml.) and to the resulting aqueous solution
  6. additionwas added ethyl acetate (60 ml.)
  7. stirringwith stirring
  8. customto precipitate powder
  9. filtrationThe precipitates were collected by filtration
  10. stirringwell stirred in ethyl acetate (50 ml.)
  11. customto remove impurities
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-58c9518599ea4ff78b2e118a779be61a
Source dataset
uspto-grants-1983_10
Patent number
US04411898

Reaction notes

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