Trifluoroacetic acid → HCID 131719786, compound

HRID 1292084Notes

Reaction equation

HRID 1292084 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:33](=[O:34])[N:13]3[C:14]([C:30]([O-:32])=[O:31])=[C:15]([S:18][C:19]4[N:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=5)[N:22]=[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.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:33](=[O:34])[N:13]3[C:14]([C:30]([OH:32])=[O:31])=[C:15]([S:18][C:19]4[N:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=5)[N:22]=[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

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131719787HCID 131719787, compound

Product 1

HCID 131719786HCID 131719786, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring suspension of (7R)-7-[(phenylacetyl)amino]-3-(1-(pyrid-2-yl)pyrazol-5-ylthio)-3-cephem-4-carboxylate, 4-methoxybenzyl ester (100 mg, 0.16 mmol) and anisole (0.6 mL) in dichloromethane (1.2 mL) at 0° C. was added trifluoroacetic acid (1.2 mL). After 30 min at 0° C., the solvent was removed with a rotary evaporator. The residue was dissolved in ethyl acetate, and was extracted with saturated aqueous sodium bicarbonate. The aqueous extracts were washed with ether, and were then acidified to pH 4-5 using aqueous HCl. This was extracted with ethyl acetate, and the organic extracts were washed with water and brine, and were dried (sodium sulfate) and concentrated. The resulting oil was triturated with hexane to afford the title compound (60 mg, 75%) as a pale yellow solid. 1H NMR (acetone-d6) δ3.55 (d, 1, J=18), 3.63 (d, 1, J=16), 3.71 (d, 1, J=16), 3.79 (d, 1, J=18), 5.25 (d, 1, J=4), 5.89 (dd, 1, J=4, 9), 6.44 (d, 1, J=2), 7.2-7.4 (m, 6), 7.78 (d, 1, J=2), 7.92 (d, 1, J=10), 8.02 (dt, 1, J=2, 10), 8.18 (d, 1, J=9), 8.48 (dd, 1, J=2, 8).

Workup

  1. customthe solvent was removed with a rotary evaporator
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. extractionwas extracted with saturated aqueous sodium bicarbonate
  4. washThe aqueous extracts were washed with ether
  5. extractionThis was extracted with ethyl acetate
  6. washthe organic extracts were washed with water and brine
  7. dry with materialwere dried (sodium sulfate)
  8. concentrationconcentrated
  9. customThe resulting oil was triturated with hexane

Sources & evidence

ORD record
ord-e108d030a90f4abaa9746b6439a67b53
Source dataset
uspto-grants-1998_05
Patent number
US05756493

Reaction notes

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