Formic Acid → 3-(1-methyl-1H-tetrazol-5-yl) thiomethyl-3-cephem-4-carboxylic acid

HRID 434384Notes

Reaction equation

HRID 434384 reaction equation
C(NC1SC=C(C(=NOC)C(N[CH:30]2[C:48](=[O:49])[N:32]3[C:33]([C:45]([OH:47])=[O:46])=[C:34]([CH2:37][S:38][C:39]4[N:43]([CH3:44])[N:42]=[N:41][N:40]=4)[CH2:35][S:36][C@H:31]23)=O)N=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)=O>O>[CH3:44][N:43]1[C:39]([S:38][CH2:37][C:34]2[CH2:35][S:36][C@@H:31]3[CH2:30][C:48](=[O:49])[N:32]3[C:33]=2[C:45]([OH:47])=[O:46])=[N:40][N:41]=[N:42]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 1317117547-[{2-(2-Tritylamino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-3-[(1-methyl-tetrazol-5-yl)-thiomethyl]-ceph-3-eme-4-carboxylic acid

Product 1

HCID 1186430063-(1-methyl-1H-tetrazol-5-yl) thiomethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.4 g of the product of Example 3 and 5 ml of 50% aqueous formic acid was held on a water bath at 55° C. for 15 minutes and then 5 ml of water were added. The mixture was cooled and vacuum filtered and the filtrate was concentrated after the addition of 5 ml of ethanol. The residue was taken up in 5 ml of ethanol and the mixture was triturated and was vacuum filtered. The product was washed with ethanol and then ether, was vacuum filtered, dried and washed to obtain 0.557 g of pure 7-[{2-amino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-3-[(1-methyl-tetrazol-5-yl)-thiomethyl]-ceph-3-eme-4-carboxylic acid in the syn configuration.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationvacuum filtered
  3. concentrationthe filtrate was concentrated
  4. additionafter the addition of 5 ml of ethanol
  5. customthe mixture was triturated
  6. filtrationfiltered
  7. washThe product was washed with ethanol
  8. filtrationfiltered
  9. customdried
  10. washwashed

Sources & evidence

ORD record
ord-34e8cd2aa34d4b8eb2ad8d45366c7f72
Source dataset
uspto-grants-1983_08
Patent number
US04396618

Reaction notes

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