Trifluoroacetic acid → HCID 178433978, compound

HRID 1858523Notes

Reaction equation

HRID 1858523 reaction equation
C(OC([NH:8][C:9]1[S:13][N:12]=[C:11]([CH2:14][C:15]([NH:17][C@@H:18]2[C:34](=[O:35])[N:20]3[C:21]([C:31]([OH:33])=[S:32])=[C:22]([C:25]4[S:26][C:27]([CH3:30])=[N:28][N:29]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>ClCCl>[NH2:8][C:9]1[S:13][N:12]=[C:11]([CH2:14][C:15]([NH:17][C@@H:18]2[C:34](=[O:35])[N:20]3[C:21]([C:31]([OH:33])=[S:32])=[C:22]([C:25]4[S:26][C:27]([CH3:30])=[N:28][N:29]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 178433977HCID 178433977, compound

Product 1

HCID 178433978HCID 178433978, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7β-[2-(5-tert-butoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylic acid (800 mg) in dichloromethane (2.4 ml) was added trifluoroacetic acid (10.4 ml). The mixture was stirred for 30 minutes at room temperature. The reaction mixture was poured into diisopropyl ether (150 ml). The precipitate was collected by filtration and dried. The precipitate was dissolved in a mixture of aqueous sodium hydrogen carbonate (212 mg/30 ml) and tetrahydrofuran (10 ml). The solution was washed with ethyl acetate (30 ml). To the aqueous layer was added a mixture of tetrahydrofuran (15 ml) and ethyl acetate (45 ml), adjusted to pH 2 with 1N-hydrochloric acid. The organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diethyl ether to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylic acid (490 mg).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customdried
  3. dissolutionThe precipitate was dissolved in a mixture of aqueous sodium hydrogen carbonate (212 mg/30 ml) and tetrahydrofuran (10 ml)
  4. washThe solution was washed with ethyl acetate (30 ml)
  5. additionTo the aqueous layer was added
  6. additiona mixture of tetrahydrofuran (15 ml) and ethyl acetate (45 ml)
  7. washThe organic layer was washed with saturated aqueous sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-977b584a18734be5981ee9bcc8ae038a
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

Loading…