Formic Acid → HCID 131711752, compound

HRID 434383Notes

Reaction equation

HRID 434383 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:50][O:51][CH3:52])[C:27]([NH:29][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[S:43][C:42]([CH3:44])=[N:41][N:40]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)=O>O.C(N(CC)CC)C>[NH2:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:50][O:51][CH3:52])[C:27]([NH:29][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[S:43][C:42]([CH3:44])=[N:41][N:40]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 131711753HCID 131711753, compound

Product 1

HCID 131711752HCID 131711752, compoundYield 28.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
57 °C

Procedure

A mixture of 1.4 g of the product of Example 1 and 5 ml of 50% aqueous formic acid was heated at 57° C. for 15 minutes and 5 ml of water were added. The mixture was cooled to room temperature and was vacuum filtered. The product was washed with ethanol and ether to obtain 0.687 g of raw product which was dissolved in 7 ml of water and 0.2 ml of triethylamine. The mixture was vacuum filtered and the filter was rinsed. The filtrate was acidified with 0.2 ml of 50% aqueous formic acid and the mixture was stirred and vacuum filtered. The product was washed with alcohol and ether to obtain 0.275 g of 7-[{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-3-[(2-methyl-1,3,4-thiadiazol-5-yl)-thiomethyl]-ceph-3-eme-4-carboxylic acid with a syn configuration.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe product was washed with ethanol and ether
  4. customto obtain 0.687 g of raw product which
  5. filtrationfiltered
  6. washthe filter was rinsed
  7. filtrationvacuum filtered
  8. washThe product was washed with alcohol and ether

Sources & evidence

ORD record
ord-28a2137034cd4f8fb3ed6b9790a10e08
Source dataset
uspto-grants-1983_08
Patent number
US04396618

Reaction notes

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