HCID 131711165, compound → HCID 131711164, compound

HRID 866875Notes

Reaction equation

HRID 866875 reaction equation
C(OC([NH:8][CH2:9][C:10]([NH:12][N:13]=[CH:14][C:15]1[CH2:16][S:17][C@@H:18]2[CH:25]([NH:26][C:27](=[O:34])[CH2:28][C:29]3[S:30][CH:31]=[CH:32][CH:33]=3)[C:24](=[O:35])[N:19]2[C:20]=1[C:21]([OH:23])=[O:22])=[O:11])=O)(C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[NH2:8][CH2:9][C:10]([NH:12][N:13]=[CH:14][C:15]1[CH2:16][S:17][C@@H:18]2[CH:25]([NH:26][C:27](=[O:34])[CH2:28][C:29]3[S:30][CH:31]=[CH:32][CH:33]=3)[C:24](=[O:35])[N:19]2[C:20]=1[C:21]([OH:23])=[O:22])=[O:11]

Participants

4

Reactant 1

HCID 131711165HCID 131711165, compound

Product 1

HCID 131711164HCID 131711164, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of 3-[2-(N-tertiary butoxycarbonylglycyl)hydrazono]methyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid (120 mg) in a mixture of anisole (0.6 ml) and trifluoroacetic acid (1.2 ml) is kept at 0° C for 1 hour. The reaction mixture is concentrated to remove trifluoroacetic acid, and the obtained residue is diluted with ether. The separated crystals are washed with ether and water and dried to give 3-(2-glycylhydrazono)methyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid (60 mg). m.p. 204°-209° C (decomposition). Yield: 62%. IR: νmax Nujol 3260, 1767, 1660, 1600, 1585cm-1. UV: νmaxEtOH 235nm; 316nm (Saturated solution). NMR: δd 6-DMSO 3.58s2H, 3.9dd2H, 5.17d(4Hz)1H, 5.75dd(8;4Hz)1H, 6.80-7.47m3H, 8.20s1H, 9.13d(8Hz)1H.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customto remove trifluoroacetic acid
  3. additionthe obtained residue is diluted with ether
  4. washThe separated crystals are washed with ether and water
  5. customdried

Sources & evidence

ORD record
ord-78234cc7765e49dca0a9a34991a83187
Source dataset
uspto-grants-1978_07
Patent number
US04101658

Reaction notes

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