Trifluoroacetic acid → HCID 178520259, compound

HRID 249616Notes

Reaction equation

HRID 249616 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:21]3[S:20][CH2:19][C:18]=2[CH2:36][S:37][C:38]2[N:39]=[N:40][NH:41][CH:42]=2)=[S:16])C2C=CC=CC=2)C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[C:28]1([CH2:27][C:26]([NH:25][C@@H:24]2[C:23](=[O:35])[N:22]3[C:17]([C:15]([OH:14])=[S:16])=[C:18]([CH2:36][S:37][C:38]4[N:39]=[N:40][NH:41][CH:42]=4)[CH2:19][S:20][C@H:21]23)=[O:34])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 178520260HCID 178520260, compound

Product 1

HCID 178520259HCID 178520259, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 7β-phenylacetylamino-3-(1,2,3-triazol -4-yl)thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (186 mg : 0.296 mMol ) in dichloromethane (3 ml) under ice cooling is added anisole (0.45 ml) and trifluoroacetic acid (0.45 ml), and the mixture is stirred for 1 hour 40 minutes. The reaction mixture is concentrated, triturated with hexane, and washed with ethyl acetate to give 7β- phenylacetylamino-3-(1,2,3-triazol-4-yl) thiomethylthio-3-cephem-4- carboxylic acid as white solid (67 mg). Yield : 49%.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customtriturated with hexane
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-a42eb6a74e6044128da60439f7bcbe02
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

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