Trifluoroacetic acid → HCID 86585661, compound

HRID 1358918Notes

Reaction equation

HRID 1358918 reaction equation
C([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[S:25][C:26]1[S:30][N:29]=[N:28][CH:27]=1)[C@H:20]([NH:31][C:32](=[O:62])[C:33]([C:55]1[N:56]=[C:57]([NH2:61])[S:58][C:59]=1[Cl:60])=[N:34][O:35]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:19]2=[O:63])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[NH2:61][C:57]1[S:58][C:59]([Cl:60])=[C:55]([C:33](=[N:34][OH:35])[C:32]([NH:31][C@@H:20]2[C:19](=[O:63])[N:18]3[CH:21]2[S:22][CH2:23][C:24]([S:25][C:26]2[S:30][N:29]=[N:28][CH:27]=2)=[C:17]3[C:15]([OH:16])=[O:14])=[O:62])[N:56]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86585662HCID 86585662, compound

Product 1

HCID 86585661HCID 86585661, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (7R)-7-[2-(2-amino-5-chlorothiazol-4-yl)-2-trityloxyiminoacetylamino]-8-oxo-3-([1,2,3]thiadiazol-5-ylsulfanyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (570 mg, 0.61 mmol) in dichloromethane (5 mL) was added triethylsilane (2.5 mL) followed by addition of trifluoroacetic acid (5 mL). After 30 min at 0° C. the reaction mixture was concentrated under vacuum and disopropyl ether was added to the oily residue. The title compound precipitated and was filtered, washed with diisopropyl ether and dried under vacuum (380 mg). The crude product was dissolved in water/1.0 M aqueous sodium bicarbonate. The solution was loaded onto an HP20 column and inorganics were removed by washing the column thoroughly with water. The title compound was isolated by eluting with 4:1 acetonitrile/water mixture, removing acetonitrile under reduced pressure and lyophilizing the residue (145 mg, 43%).

Workup

  1. concentrationAfter 30 min at 0° C. the reaction mixture was concentrated under vacuum and disopropyl ether
  2. additionwas added to the oily residue
  3. customThe title compound precipitated
  4. filtrationwas filtered
  5. washwashed with diisopropyl ether
  6. customdried under vacuum (380 mg)
  7. dissolutionThe crude product was dissolved in water/1.0 M aqueous sodium bicarbonate
  8. customwere removed
  9. washby washing the column thoroughly with water

Sources & evidence

ORD record
ord-5ee981ef3a284df49fb9f7758450a653
Source dataset
uspto-grants-2003_07
Patent number
US06599893B2

Reaction notes

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