Trifluoroacetic acid → HCID 86585654, compound

HRID 1358913Notes

Reaction equation

HRID 1358913 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][C:27]=1[CH3:31])[C@H:20]([NH:32][C:33](=[O:63])[C:34]([C:56]1[N:57]=[C:58]([NH2:62])[S:59][C:60]=1[Cl:61])=[N:35][O:36]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:19]2=[O:64])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[NH2:62][C:58]1[S:59][C:60]([Cl:61])=[C:56]([C:34](=[N:35][OH:36])[C:33]([NH:32][C@@H:20]2[C:19](=[O:64])[N:18]3[CH:21]2[S:22][CH2:23][C:24]([S:25][C:26]2[S:30][N:29]=[N:28][C:27]=2[CH3:31])=[C:17]3[C:15]([OH:16])=[O:14])=[O:63])[N:57]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86585655HCID 86585655, compound

Product 1

HCID 86585654HCID 86585654, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (7R)-7-[2-(2-amino-5-chlorothiazol-4-yl)-2-trityloxyiminoacetylamino]-3-(4-methyl-[1,2,3]thiadiazol-5-ylsulfanyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene 2-carboxylic acid benzhydryl ester (990 mg, 1.05 mmol) in dichloromethane (21 mL) was added triethylsilane (11 mL) followed by addition of trifluoroacetic acid (21 mL). After 1 hr at room temperature the reaction mixture was concentrated under vacuum. Disopropyl ether was added to the oily residue. The title compound precipitated and was filtered, washed with additional diisopropyl ether and dried under vacuum (528 mg, 95%).

Workup

  1. concentrationAfter 1 hr at room temperature the reaction mixture was concentrated under vacuum
  2. additionDisopropyl ether was added to the oily residue
  3. customThe title compound precipitated
  4. filtrationwas filtered
  5. washwashed with additional diisopropyl ether
  6. customdried under vacuum (528 mg, 95%)

Sources & evidence

ORD record
ord-fa13335a73c04906b75e3a8ad9cb29b0
Source dataset
uspto-grants-2003_07
Patent number
US06599893B2

Reaction notes

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