Trifluoroacetic acid → HCID 70632245, compound

HRID 1578890Notes

Reaction equation

HRID 1578890 reaction equation
[CH2:1]([C:3]1[CH2:4][S:5][C@@H:6]2[CH:17]([NH:18][C:19](=[O:26])[CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[C:16](=[O:27])[N:7]2[C:8]=1[C:9]([O:11]C(C)(C)C)=[O:10])[CH3:2].FC(F)(F)C(O)=O>>[CH2:1]([C:3]1[CH2:4][S:5][C@@H:6]2[CH:17]([NH:18][C:19](=[O:26])[CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[C:16](=[O:27])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10])[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131710052HCID 131710052, compound

Product 1

HCID 70632245HCID 70632245, compoundYield 85.7%

Procedure

t-Butyl 3-ethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate (23 mg) was treated with trifluoracetic acid at room temperature for 1 hour. The excess trifluoroacetic acid was distilled off azeotropically with dry benzene to give the free acid (XVII) as a gum (17 mg) νmax (CHCl3) 1770, 1705, 1680 cm-1The minimum inhibitory concentrations of this compound required to inhibit the growth of five typical Gram-positive bacteria are tabulated below:

Workup

  1. distillationThe excess trifluoroacetic acid was distilled off azeotropically with dry benzene

Sources & evidence

ORD record
ord-3e3736a6801048d294173fdd6582123e
Source dataset
uspto-grants-1976_02
Patent number
US03939157

Reaction notes

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