HCID 21070796, compound → HCID 21070679, compound

HRID 1371358Notes

Reaction equation

HRID 1371358 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][CH:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:34][CH2:33][CH2:32][C@H:24]4C(OC(C)(C)C)=O)=[CH:19][CH:18]=3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1>ClCCl.FC(F)(F)C(O)=O>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][CH:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:34][CH2:33][CH2:32][CH2:24]4)=[CH:19][CH:18]=3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 21070796HCID 21070796, compound

Product 1

HCID 21070679HCID 21070679, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

780 mg (1.54 mmol) of tert-butyl 1-{4-[5-({[(5-chloro-2-thienyl)carbonyl]amino}-methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}prolinate are dissolved in 6 ml of dichloromethane and 9 ml of trifluoroacetic acid, and the mixture is stirred at 40° C. for two days. The reaction mixture is then concentrated and stirred with ether and 2N aqueous sodium hydroxide solution. The aqueous phase is concentrated and stirred with ether and 2N hydrochloric acid. The organic phase of this extraction is dried over MgSO4, filtered and concentrated. The crude product is chromatographed over silica gel (CH2Cl2/EtOH/conc. aqu. NH3 sol.=100/1/0.1 to 20/1/0.1). This gives 280 mg (40% of theory) of the product.

Workup

  1. concentrationThe reaction mixture is then concentrated
  2. concentrationThe aqueous phase is concentrated
  3. stirringstirred with ether and 2N hydrochloric acid
  4. extractionThe organic phase of this extraction
  5. dry with materialis dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is chromatographed over silica gel (CH2Cl2/EtOH/conc. aqu. NH3 sol.=100/1/0.1 to 20/1/0.1)

Sources & evidence

ORD record
ord-e0339d3d74b84a3c8501863e1871d201
Source dataset
uspto-grants-2007_01
Patent number
US07157456B2

Reaction notes

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