tert-Butyl 4-[5-(4-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-2-pyridinyl]-1-piperazinecarboxylate → HCID 10136449, compound

HRID 1446084Notes

Reaction equation

HRID 1446084 reaction equation
[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[CH:20][C:21]([N:24]4[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]4)=[N:22][CH:23]=3)=[C:14]([F:37])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2]>C(Cl)Cl.FC(F)(F)C(O)=O>[F:37][C:14]1[CH:13]=[C:12]([N:8]2[CH2:7][C@H:6]([CH2:5][NH:4][C:1](=[O:3])[CH3:2])[O:10][C:9]2=[O:11])[CH:17]=[CH:16][C:15]=1[C:18]1[CH:23]=[N:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 68549816tert-Butyl 4-[5-(4-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-2-pyridinyl]-1-piperazinecarboxylate

Product 1

HCID 10136449HCID 10136449, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 4-[5-(4-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-2-pyridinyl]-1-piperazinecarboxylate (0.191 g, 0.372 mmol) in DCM (10 mL) and trifluoroacetic acid (10 mL) was stirred at room temperature for 3 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 1 M NaOH solution. The organic layer was dried and evaporated to give the titled compound (0.150 g, 98%) as a colourless foam. APCI MS m/z 414 (M+H). 1H NMR (400 MHz, DMSO-d6) δ 8.30 (s, 1H), 8.22 (t, J=5.8 Hz, 1H), 7.72 (bdt, J=9.0, 2.1 Hz, 1H), 7.52-7.60 (m, 2H), 7.38 (dd, J=8.6, 2.1 Hz, 1H), 6.89 (d, J=9.0 Hz, 1H), 4.72-4.80 (m, 1H), 4.16 (t, J=9.0 Hz, 1H), 3.78 (dd, J=9.1, 6.7 Hz, 1H), 3.41-3.51 (m, 6H), 2.80-2.85 (m, 4H), 1.84 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc and 1 M NaOH solution
  3. customThe organic layer was dried
  4. customevaporated

Sources & evidence

ORD record
ord-46a8c0a4d1e340e9bd0a8073366aa3ae
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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