Trifluoroacetic acid → HCID 131711162, compound

HRID 866874Notes

Reaction equation

HRID 866874 reaction equation
C(OC([NH:8][N:9]=[CH:10][C:11]1[CH2:12][S:13][C@@H:14]2[CH:21]([NH:22][C:23](=[O:30])[CH2:24][C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)[C:20](=[O:31])[N:15]2[C:16]=1[C:17]([OH:19])=[O:18])=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[N:9](=[CH:10][C:11]1[CH2:12][S:13][C@@H:14]2[CH:21]([NH:22][C:23](=[O:30])[CH2:24][C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)[C:20](=[O:31])[N:15]2[C:16]=1[C:17]([OH:19])=[O:18])[NH2:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131711163HCID 131711163, compound

Product 1

HCID 131711162HCID 131711162, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-tertiary butoxycarbonylhydrazono)methyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid (247 mg) in methylene chloride (1 ml) are added anisole (0.6 ml) and trifluoroacetic acid (0.6 ml), and the mixture is kept at room temperature for 1 hour. After removing trifluoroacetic acid and methylene chloride, the reaction mixture is diluted with ether. The separated cyrstals are collected by filtration and dried to give 3-hydrazonomethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid in nearly quantitative yield. m.p. 164°-169° C (decomposition). IR: νmaxNujol 3260, 1787, 1657, 1542cm-1. UV: λmaxCH3OH 230.5nm(ε=12900); 304nm(ε=6900); 402nm(ε=12400). NMR: δd 6-DMSO (60MHz) 3.79s2H, 3,84d(12Hz)2H, 5.20d(5Hz)1H, 5.84dd(8;5Hz)1H, 6.8-7.5m3H, 7.55s+7.78s1H, 9.12d(8Hz)1H. [α]D23.5 +66.2°(c=0.5022, DMSO).

Workup

  1. customAfter removing trifluoroacetic acid and methylene chloride
  2. additionthe reaction mixture is diluted with ether
  3. filtrationThe separated cyrstals are collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-a33812a545b24c75839072caa9533966
Source dataset
uspto-grants-1978_07
Patent number
US04101658

Reaction notes

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