Trifluoroacetic acid → HCID 86754241, compound

HRID 582488Notes

Reaction equation

HRID 582488 reaction equation
C([O:14][C:15]([C:17]1[N:18]2[C@H:21]([S:22][CH2:23][C:24]=1/[CH:25]=[C:26]1/[C:27](=[O:35])[N:28]([CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:29][CH2:30]/1)[C@H:20]([NH:36]C(OC(C)(C)C)=O)[C:19]2=[O:44])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48]>ClCCl.C1(OC)C=CC=CC=1>[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].[NH2:36][C@@H:20]1[C:19](=[O:44])[N:18]2[C@@H:21]1[S:22][CH2:23][C:24](/[CH:25]=[C:26]1/[C:27](=[O:35])[N:28]([CH2:31][CH:32]([CH3:33])[CH3:34])[CH2:29][CH2:30]/1)=[C:17]2[C:15]([OH:16])=[O:14]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86754243HCID 86754243, compound

Product 1

HCID 86754241HCID 86754241, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

(E)-(6R,7R)-7-tert-Butoxycarbonylamino-3-(1-isobutyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (21.9 g, 35.0 mmol) was dissolved in 240 ml dichloromethane and 23 ml anisole. At 20° C. 120 ml trifluoroacetic acid were added dropwise while maintaining the temperature below 50° C. After complete addition the ice-bath was removed and the solution was stirred at ambient temperature for 2.5 hours The volatile material was then removed under reduced pressure and the remaining yellow oil was added slowly to 400 ml of diethyl ether, in which the product started to precipitate. After 1.5 hours the suspension was filtered under argon atmosphere and the remaining crystals were stirred in 150 ml of ethyl acetate for 2 hours. The suspension was filtered under argon giving the desired product as a yellow crystalline powder.

Workup

  1. customAt 20° C
  2. temperaturewhile maintaining the temperature below 50° C
  3. customwas removed
  4. customwas then removed under reduced pressure
  5. additionthe remaining yellow oil was added slowly to 400 ml of diethyl ether, in which the product
  6. customto precipitate
  7. filtrationAfter 1.5 hours the suspension was filtered under argon atmosphere
  8. stirringthe remaining crystals were stirred in 150 ml of ethyl acetate for 2 hours
  9. filtrationThe suspension was filtered under argon giving the desired product as a yellow crystalline powder

Sources & evidence

ORD record
ord-f12a858473fa47849d9502d559d39477
Source dataset
uspto-grants-1999_07
Patent number
US05925632

Reaction notes

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