Trifluoroacetic acid → HCID 178432604, compound

HRID 1858516Notes

Reaction equation

HRID 1858516 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:44](=[O:45])[N:13]3[C:14]([C:28]([O:30]C(C4C=CC=CC=4)C4C=CC=CC=4)=[S:29])=[C:15]([C:18]4[S:19][C:20]([CH2:24][C:25](=[O:27])[NH2:26])=[C:21]([CH3:23])[N:22]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>ClCCl>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:44](=[O:45])[N:13]3[C:14]([C:28]([OH:30])=[S:29])=[C:15]([C:18]4[S:19][C:20]([CH2:24][C:25](=[O:27])[NH2:26])=[C:21]([CH3:23])[N:22]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131722165HCID 131722165, compound

Product 1

HCID 178432604HCID 178432604, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of benzhydryl 7β-(2-phenylacetamido)-3-(5-carbamoylmethyl-4-methylthiazol-2-yl)thio-3-cephem-4-carboxylate (0.80 g), anisole (0.80 ml) and dichloromethane (2.40 ml) was added trifluoroacetic acid (1.60 ml) at 15° C. After stirring at room temperature for 1 hour, the solution was poured into diisopropyl ether. The resulting precipitate was collected by filtration, added to a mixture of tetrahydrofuran and water, and adjusted to pH 7.5 with an aqueous sodium bicarbonate. The separated aqueous solution was washed with ethyl acetate and adjusted to pH 3.0 with 1N-hydrochloric acid. The resulting crystal was collected by filtration and washed with water to give 7β-(2-phenylacetamido)-3-(5-carbamoylmethyl-4-methylthiazol-2-yl)thio-3-cephem-4-carboxylic acid (445 mg).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. additionadded to a mixture of tetrahydrofuran and water
  3. washThe separated aqueous solution was washed with ethyl acetate
  4. filtrationThe resulting crystal was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-6eb88ed84e3f4e57b67e014754691c2f
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

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