HCID 86736114, compound → HCID 86736113, compound

HRID 1448578Notes

Reaction equation

HRID 1448578 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:30])[CH:10]2[NH:14][C:15](=[O:29])[CH:16]([C:24]([O:26]CC)=[O:25])[N:17]2[CH:21]=[CH:20][CH:19]=[C:18]2[CH:22]=[O:23])[C:7]=1[C:31]([O:33]C(C)(C)C)=[O:32])(=[O:3])[CH3:2]>FC(F)(F)C(O)=O>[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:30])[CH:10]2[NH:14][C:15](=[O:29])[CH:16]([C:24]([OH:26])=[O:25])[N:17]2[CH:21]=[CH:20][CH:19]=[C:18]2[CH:22]=[O:23])[C:7]=1[C:31]([OH:33])=[O:32])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 86736114HCID 86736114, compound

Product 1

HCID 86736113HCID 86736113, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

3-[(Acetyloxy)methyl]-7-[[2-carboethoxy-2-(2-formyl-1-pyrryl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, tert-butyl ester, 0.05 m, is added to 50 ml of trifluoroacetic acid which is maintained at 0° C. The reaction mixture is stirred at 0° C. for 15 minutes and then at 10° C. for 15 minutes. The trifluoroacetic acid is removed in vacuo, the temperature of the mixture not rising above 20° C. The residue was taken up in methanol-water (4:1) and the pH adjusted to about 4 with ammonium hydroxide. The precipitate is filtered and the filtrate is concentrated and cooled to give the title compound.

Workup

  1. waitat 10° C. for 15 minutes
  2. customThe trifluoroacetic acid is removed in vacuo
  3. customrising above 20° C
  4. filtrationThe precipitate is filtered
  5. concentrationthe filtrate is concentrated
  6. temperaturecooled

Sources & evidence

ORD record
ord-5000132284cf4cc787c48a3e012a4e15
Source dataset
uspto-grants-1979_12
Patent number
US04180660

Reaction notes

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