Trifluoroacetic acid → HCID 10649207, compound

HRID 1939892Notes

Reaction equation

HRID 1939892 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([O-:28])=[O:27])=[C:15]([S:18][C:19]4[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C1(O)C=CC=CC=1>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([OH:28])=[O:27])=[C:15]([S:18][C:19]4[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131719783HCID 131719783, compound

Product 1

HCID 10649207HCID 10649207, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 996PhenolSolvent

Procedure

To a solution of (7R)-7-[(phenylacetyl)amino]-3-(4-bromophenylthio)-3-cephem-4-carboxylate, benzhydryl ester (80 mg, 0.12 mmol) in phenol (230 mg) at 45° was added trifluoroacetic acid (9 μL). After 1.5 h, the volatiles are removed with a rotary evaporator, and the residue is triturated with isopropanol/hexane. The resulting white solid was washed with ether and dried in vacuo, affording 48 mg (79%) of the title compound. 1H NMR (acetone-d6) δ3.67 (d, 1H, J=16), 3.75 (d, 1H, J=16), 3.64 (d, 1H, J=18), 3.67 (d, 1H, J=18), 5.25 (d, 1H, J=5), 5.92 (d, 1H, J=5), 7.2-7.7 (m, 9H); IR (KBr) 1347, 1386, 1606, 1756, 3276 cm-1.

Workup

  1. customthe volatiles are removed with a rotary evaporator
  2. customthe residue is triturated with isopropanol/hexane
  3. washThe resulting white solid was washed with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-934940747c3f4011ac4475cf940467ba
Source dataset
uspto-grants-1997_12
Patent number
US05698547

Reaction notes

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