Trifluoroacetic acid → HCID 178511446, compound

HRID 249619Notes

Reaction equation

HRID 249619 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:43])[C@@H:24]([NH:25][C:26](=[O:42])[CH:27]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[NH:28]C(OC(C)(C)C)=O)[C@H:21]3[S:20][CH2:19][C:18]=2[S:44][CH:45](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:46][C:47]2[N:48]=[N:49][NH:50][CH:51]=2)=[O:16])C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)C(O)=O.C(OCC)(=O)C>C1(OC)C=CC=CC=1.ClCCl>[C:36]1([CH:27]([C:26]([NH:25][C@@H:24]2[C:23](=[O:43])[N:22]3[C:17]([C:15]([OH:16])=[O:14])=[C:18]([S:44][CH2:45][S:46][C:47]4[N:48]=[N:49][NH:50][CH:51]=4)[CH2:19][S:20][C@H:21]23)=[O:42])[NH2:28])[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 178453837HCID 178453837, compound

Product 1

HCID 178511446HCID 178511446, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of 7β-(N-t-butoxycarbonyl-2-phenylglycylamino) -3- (trityl-1,2,3-triazol-4-ylthiomethylthio) -3-cephem-4-carboxylic acid diphenylmethyl ester (480 mg : 0.487 mMol.) in a mixture of anisole (1.2 ml) and dichloromethane (3 ml) under ice cooling is added trifluoro- acetic acid (3 ml), and the mixture is stirred under ice cooling for 30 minutes and at room temperature for 50 minutes. The reaction mixture is shaken with ice water and ethyl acetate under ice cooling. The aqueous layer is taken, concentrated to remove the remaining organic solvents under reduced pressure, and subjected to column chromatography over styrene-divinylbenzene copolymer resin (methanol : water=4:1). The residue is pulverized from ethyl acetate to give 7β-(2-phenylglycylamino)-3-(1,2,3-triazol -4-ylthiomethylthio)-3-cephem-4-carboxylic acid (157 mg) as white powder. Yield: 67%.

Workup

  1. concentrationconcentrated
  2. customto remove the remaining organic solvents under reduced pressure

Sources & evidence

ORD record
ord-3b2470d23ee9439a9982dc3a201ebf5c
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

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