Trifluoroacetic acid → HCID 67657557, compound

HRID 1451219Notes

Reaction equation

HRID 1451219 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:30](=[O:31])[N:13]3[C:14]([C:27]([O-:29])=[O:28])=[C:15]([S:18][C:19]4[C:20]([C:25]#[N:26])=[N:21][CH:22]=[CH:23][CH:24]=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>ClCCl>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:30](=[O:31])[N:13]3[C:14]([C:27]([OH:29])=[O:28])=[C:15]([S:18][C:19]4[C:20]([C:25]#[N:26])=[N:21][CH:22]=[CH:23][CH:24]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131719784HCID 131719784, compound

Product 1

HCID 67657557HCID 67657557, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (7R)-7-[(phenylacetyl)amino]-3-(2-cyanopyrid-3-ylthio)-3-cephem-4-carboxylate, 4-methoxybenzyl ester (158 mg, 0.277 mmol) and anisole (0.4 mL) in dichloromethane (1 mL) at 0° C. was added trifluoroacetic acid (1 mL). After 1 h at 0° C., the solvent was removed with a rotary evaporator, and the residue was triturated with ether, filtered, and dried, affording 104 mg (83%) of the title compound. 1H NMR (CDCl3) δ3.15 (d, 1, J=18), 3.54 (d, 1, J=18), 3.65 (d, 1, J=16), 3.69 (d, 1, J=16), 5.07 (d, 1, J=4), 5.89 (dd, 1, J=4, 9), 6.18 (d, 1, J=9), 7.2-7.4 (m, 5), 7.53 (dd, 1, J=5, 8), 7.90 (d, 1, J=8), 8.66 (d, 1, J=5).

Workup

  1. customthe solvent was removed with a rotary evaporator
  2. customthe residue was triturated with ether
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-d3595b2910794ab7b73e429c8774c2bb
Source dataset
uspto-grants-1997_02
Patent number
US05604218

Reaction notes

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