Trifluoroacetic acid → HCID 131716132, compound

HRID 1607948Notes

Reaction equation

HRID 1607948 reaction equation
FC(F)(F)C([O-])=O.O1CCCCC1[O:14][N:15]=[C:16]([C:53]1[N:54]=[C:55]([NH:58]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:56][CH:57]=1)[C:17]([NH:19][CH:20]1[C:51](=[O:52])[N:22]2[C:23]([C:35]([O:37]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:36])=[C:24]([CH2:27][N+:28]3([CH2:33][CH3:34])[CH2:32][CH2:31][CH2:30][CH2:29]3)[CH2:25][S:26][C@H:21]12)=[O:18].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>ClCCl>[NH2:58][C:55]1[S:56][CH:57]=[C:53]([C:16](=[N:15][OH:14])[C:17]([NH:19][CH:20]2[C:51](=[O:52])[N:22]3[C:23]([C:35]([O-:37])=[O:36])=[C:24]([CH2:27][N+:28]4([CH2:33][CH3:34])[CH2:32][CH2:31][CH2:30][CH2:29]4)[CH2:25][S:26][C@H:21]23)=[O:18])[N:54]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131716134HCID 131716134, compound

Product 1

HCID 131716132HCID 131716132, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzhydryl 7-[2-(2-tetrahydropyranyl)oxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(1-ethyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate trifluoroacetate (syn isomer) (4.0 g) in dichloromethane (12 ml) were added anisole (4 ml) and trifluoroacetic acid (8 ml) under ice-cooling. After stirring for 4 hours at room temperature, the mixture was poured into diisopropyl ether (250 ml). The resulting precipitate was collected by filtration, washed with diisopropyl ether, and dissolved in 5% sodium bicarbonate solution. The aqueous solution was adjusted to pH 2.5 with 1N hydrochloric acid, andsubjected to column chromatography on non-ionic adsorption resin "HP-20". The desired product was eluted with 5% isopropyl alcohol and the eluate was concentrated and lyophilized to give 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(1-ethyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate (syn isomer) (0.30 g).

Workup

  1. temperaturecooling
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with diisopropyl ether
  4. dissolutiondissolved in 5% sodium bicarbonate solution
  5. washThe desired product was eluted with 5% isopropyl alcohol
  6. concentrationthe eluate was concentrated

Sources & evidence

ORD record
ord-e1a5d0e66b9a44a698b45da8bc4706ba
Source dataset
uspto-grants-1989_09
Patent number
US04868174

Reaction notes

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