Trifluoroacetic acid → 3-[(Acetyloxy)methyl]-7-[[2-carboxy-2-(1-pyrryl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 26321Notes

Reaction equation

HRID 26321 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:28])[CH:10]2[NH:14][C:15](=[O:27])[CH:16]([C:22]([O:24]CC)=[O:23])[N:17]2[CH:21]=[CH:20][CH:19]=[CH:18]2)[C:7]=1[C:29]([OH:31])=[O:30])(=[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:28])[CH:10]2[NH:14][C:15](=[O:27])[CH:16]([C:22]([OH:24])=[O:23])[N:17]2[CH:21]=[CH:20][CH:19]=[CH:18]2)[C:7]=1[C:29]([OH:31])=[O:30])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 706050383-[(Acetyloxy)methyl]-7-[[2-carboethoxy-2-(1-pyrryl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid

Product 1

HCID 706051763-[(Acetyloxy)methyl]-7-[[2-carboxy-2-(1-pyrryl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Temperature
0 °C

Procedure

3-[(Acetyloxy)methyl]-7-[[2-carboethoxy-2-(1-pyrryl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid is added to trifluoroacetic acid (TFA) maintained at 0° C. This mixture is stirred for about 30 minutes, warmed to about 20° C. for about 30 minutes and then warmed (maximum of 25° C.) under vacuum to remove the TFA. The acid is taken up in ethyl acetate. The ethyl acetate is washed with water, dried over magnesium sulfate, filtered and partially concentrated. The title compound was recovered from the solvent by filtration.

Workup

  1. temperaturewarmed to about 20° C. for about 30 minutes
  2. temperaturewarmed (maximum of 25° C.) under vacuum
  3. customto remove the TFA
  4. washThe ethyl acetate is washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationpartially concentrated
  8. filtrationThe title compound was recovered from the solvent by filtration

Sources & evidence

ORD record
ord-7bbe3446b3c64ee09df72ed03dfecd10
Source dataset
uspto-grants-1979_04
Patent number
US04148998

Reaction notes

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