Trifluoroacetic acid → HCID 57271418, compound

HRID 653282Notes

Reaction equation

HRID 653282 reaction equation
C1(OC)C=CC=CC=1.[NH2:9][C:10]1[S:11][CH:12]=[C:13]([C:15](=[N:33][O:34][C:35]([CH3:53])([C:37]([O:39]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:38])[CH3:36])[C:16]([NH:18][C@H:19]2[C@@H:22]([CH2:23][O:24][C:25](=[O:27])[NH2:26])[N:21]([S:28]([O-:31])(=[O:30])=[O:29])[C:20]2=[O:32])=[O:17])[N:14]=1.[Na+].FC(F)(F)C(O)=O>CCOCC>[NH2:9][C:10]1[S:11][CH:12]=[C:13]([C:15](=[N:33][O:34][C:35]([CH3:53])([C:37]([OH:39])=[O:38])[CH3:36])[C:16]([NH:18][C@H:19]2[C@@H:22]([CH2:23][O:24][C:25](=[O:27])[NH2:26])[N:21]([S:28]([OH:31])(=[O:30])=[O:29])[C:20]2=[O:32])=[O:17])[N:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86740459HCID 86740459, compound

Product 1

HCID 57271418HCID 57271418, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-20 °C

Procedure

To 1 ml of anisole is added 250 mg of sodium cis-3-[2-(2-amino-4-thiazolyl)-2-(1-methyl-1-benzhydryloxycarbonylethyloxyimino)acetamido]-4-carbamoyloxymethyl-2-oxoazetidine-1-sulfonate (syn-isomer) and under stirring at -20° C., 5 ml of trifluoroacetic acid is added dropwise. The mixture is stirred at -15° C. for 30 minutes, after which 10 ml of ether and 10 ml of petroleum ether are added. The resultant powder is recovered by centrifugation are dissolved in water. To the solution is Dowex 50W (H-form) resin, followed by stirring. The resin is filtered off and the filtrate is concentrated and purified by chromatography using an Amberlite XAD-2 (eluent: water, 100 ml; 10% ethanol, 100 ml; 30% ethanol, 100 ml and then 40% ethanol, 50 ml) and the fractions of 30% ethanol and 40% ethanol are lyophilized to give cis-3-[2-(2-amino-4-thiazolyl)-2-(1-methyl-1-carboxyethyloxyimino)acetamido]-4-carbamoyloxymethyl-2-oxoazetidine-1-sulfonic acid (syn-isomer).

Workup

  1. stirringThe mixture is stirred at -15° C. for 30 minutes
  2. customThe resultant powder is recovered by centrifugation
  3. dissolutionare dissolved in water
  4. stirringby stirring
  5. filtrationThe resin is filtered off
  6. concentrationthe filtrate is concentrated
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-0a8ccfc84f8343abb56f696639db4f73
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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