Trifluoroacetic acid → HCID 131711675, compound

HRID 2052176Notes

Reaction equation

HRID 2052176 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:5]([NH:7][CH:8]1[C:39](=[O:40])[N:10]2[C:11]([C:23]([O:25]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:24])=[C:12]([C:15]3[S:16][C:17]([N:20]([CH3:22])[CH3:21])=[N:18][N:19]=3)[CH2:13][S:14][C@H:9]12)=[O:6].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[CH3:1][O:2][N:3]=[C:4]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:5]([NH:7][CH:8]1[C:39](=[O:40])[N:10]2[C:11]([C:23]([OH:25])=[O:24])=[C:12]([C:15]3[S:16][C:17]([N:20]([CH3:22])[CH3:21])=[N:18][N:19]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131711676HCID 131711676, compound

Product 1

HCID 131711675HCID 131711675, compoundYield 70.7%

Procedure

A mixture of 0.11 g of benzhydryl 7-(2-methoxyimino-2-phenylacetamido)-3-(5-dimethylamino-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylate (obtained in Example 48), 2 ml of anisole and 4 ml of trifluoroacetic acid is stirred for 30 minutes at room temperature. After removal of the solvent under reduced pressure, the residue is triturated with the addition of absolute ether. The precipitates are filtered, and washed with ether to give 0.058 g of 7-(2-methoxyimino-2-phenylacetamido)-3-(5-dimethylamino-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylic acid.

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. customthe residue is triturated with the addition of absolute ether
  3. filtrationThe precipitates are filtered
  4. washwashed with ether

Sources & evidence

ORD record
ord-ff072f7bbd3549b1ae5d03942464509a
Source dataset
uspto-grants-1980_01
Patent number
US04182866

Reaction notes

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